Iminipyridine derivatives and their uses as microbiocides

ABSTRACT

Compounds of the formula I 
                         
in which the substituents are as defined in claim  1  are suitable for use as microbiocides.

This application is a continuation of U.S. Ser. No. 12/528,198, filedAug. 21, 2009 now U.S. Pat. No. 8,513,286, which is a 371 ofInternational Application No. PCT/EP2008/001315, filed Feb. 20, 2008,which claims priority from EP 07003637.1 filed Feb. 22, 2007; thecontents of all above-named applications are incorporated herein byreference.

The present invention relates to novel microbiocidally active, inparticular fungicidally active, pyridylamidine compounds. It furtherrelates to intermediates used in the preparation of these compounds, tocompositions which comprise these compounds and to their use inagriculture or horticulture for controlling or preventing infestation ofplants by phytopathogenic microorganisms, preferably fungi.

Certain phenylamidine derivatives have been proposed in the literatureas microbicidally active ingredients in pesticides. For example, WO00/46184 and WO 03/093224 disclose phenylamidines which are useful asfungicides. However, the biological properties of these known compoundsare not entirely satisfactory for controlling or preventing infestationof plants by phytopathogenic microorganisms, which is why there is aneed to provide other compounds which have microbicidal properties.There have now been found novel pyridylamidines having microbiocidalactivity.

The present invention accordingly relates to compounds of formula I

wherein

-   aa) R₁ and R₂, independently from each other, are hydrogen, cyano,    formyl, nitro, C₁-C₇alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,    C₂-C₇alkylcarbonyl, C₃-C₇alkenylcarbonyl, C₄-C₉cycloalkylcarbonyl,    C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkylthio-C₁-C₆alkyl,    C₂-C₇alkylcarbonyl-C₁-C₆alkyl, C₃-C₆alkenyloxy-C₁-C₆alkyl,    C₃-C₆alkynyloxy-C₁-C₆alkyl, benzyloxy-C₁-C₆alkyl,    C₃-C₉cycloalkyl-C₁-C₆alkyl, C₂-C₇alkyloxycarbonyl,    C₄-C₇alkenyloxycarbonyl, C₄-C₇alkynyloxycarbonyl,    C₄-C₈cycloalkyloxycarbonyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylsulfonyl, C₁-C₆alkylsulfinyl or    C₁-C₆haloalkylsulfinyl; or-   ab) R₁ and R₂, independently from each other, are    —Si(R₅₁)(R₅₂)(R₅₃), wherein R₅₁, R₅₂, R₅₃, independently of each    other, are halogen, cyano, C₁-C₆alkyl, C₂-C₆alkenyl,    C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy,    benzyl or phenyl; or-   ac) R₁ and R₂, independently from each other, are    —Si(OR₅₄)(OR₅₅)(OR₅₆), wherein R₅₄, R₅₅, R₅₆, independently of each    other, are C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₈cycloalkyl, C₃-C₆alkynyl,    benzyl or phenyl; or-   ad) R₁ and R₂, independently from each other, are phenylsulfonyl,    phenylsufinyl, phenylcarbonyl, phenoxycarbonyl, benzyl,    benzylcarbonyl or benzyloxycarbonyl; or-   ae) R₁ and R₂, independently from each other, are phenylsulfonyl,    phenylsufinyl, phenylcarbonyl, phenoxycarbonyl, benzyl,    benzylcarbonyl, benzyloxycarbonyl mono- to polysubstituted-   ae1) by substituents independently selected from the group    consisting of-   hydroxy, mercapto, halogen, cyano, azido, nitro, —SF₅, amino,    C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl,    C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl,    C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkoxyC₁-C₆alkyl,    C₁-C₆alkylthioC₁-C₆alkyl, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy,    C₃-C₆alkynyloxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylsulfonyl, benzyloxy, phenoxy, benzyl and phenyl, where    benzyloxy, phenoxy, benzyl and phenyl for their part may be mono- to    polysubstituted on the phenyl ring by substituents independently    selected from the group consisting of halogen, cyano, hydroxy,    C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or-   ae2) by substituents independently selected from the group    consisting of-   carboxy, —C(═O)—Cl, —C(═O)—F, C₂-C₇alkoxycarbonyl,    C₂-C₇alkylthiocarbonyl, C₂-C₇haloalkoxycarbonyl,    C₃-C₇alkenyloxycarbonyl, C₃-C₇haloalkenyloxycarbonyl,    C₃-C₇alkynyloxycarbonyl, benzyloxycarbonyl and phenoxycarbonyl,    where benzyloxycarbonyl and phenoxycarbonyl for their part may be    mono- to polysubstituted on the phenyl ring by substituents    independently selected form the group consisting of halogen, cyano,    hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or-   ae3) by substituents independently selected from the group    consisting of-   formyl, C₂-C₇alkylcarbonyl, C₂-C₇haloalkylcarbonyl,    C₃-C₇alkenylcarbonyl, phenylcarbonyl and benzylcarbonyl, where    phenylcarbonyl and benzylcarbonyl for their part may be mono-to    polysubstituted on the phenyl ring by substituents independently    selected form the group consisting of halogen, cyano, hydroxy,    C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or-   ae4) by substituents independently selected from the group    consisting of aminosulfonyl, C₁-C₆alkylaminosulfonyl,    N,N-di(C₁-C₆alkyl)aminosulfonyl, —C(═O)NR₅₇R₅₈, —C(═S)NR₅₇R₅₈ and    —NR₅₇R₅₈, wherein R₅₇ and R₅₈, independently of each other, are    hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl,    C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₈cycloalkyl,    C₃-C₈halocycloalkyl, phenyl or benzyl, where phenyl, benzyl for    their part may be mono- to polysubstituted on the phenyl ring by    substituents independently selected form the group consisting of    halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy,    or R₅₇ and R₅₈ together with their interconnecting nitrogen atom are    aziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino,    pyrrolidino, imidazolino, imidazolidino, triazolino, tetrazolino,    piperazino, piperidino, morpholino, thiomorpholino, each of which,    in turn, may be mono- or polysubstituted by substituents selected    from the group consisting of methyl, halogen, cyano and nitro; and    substituents at nitrogen atoms in the ring systems being other than    halogen; or-   af) either R₁ or R₂ is-   af1) hydroxy, amino, C₁-C₆alkoxy, C₃-C₆alkenyloxy,    C₃-C₈cycloalkyloxy, C₃-C₆alkynyloxy or benzyloxy; or-   af2) C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₈cycloalkyloxy,    C₃-C₆alkynyloxy, benzyloxy mono- to polysubstituted by substituents    independently selected from the group consisting of halogen, cyano,    hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy and    C₁-C₆haloalkoxy; or-   ag) R₁ and R₂, independently from each other, are C₁-C₇alkyl,    C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₇alkylcarbonyl,    C₃-C₇alkenylcarbonyl, C₄-C₉cycloalkylcarbonyl,    C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkylthio-C₁-C₆alkyl,    C₃-C₆alkenyloxy-C₁-C₆alkyl, C₂-C₆alkylcarbonyl-C₁-C₆alkyl,    C₃-C₆alkynyloxy-C₁-C₆alkyl, benzyloxy-C₁-C₆alkyl,    C₃-C₈cycloalkyl-C₁-C₆alkyl, C₂-C₇alkyloxycarbonyl,    C₄-C₇alkenyloxycarbonyl, C₄-C₇alkynyloxycarbonyl or    C₄-C₉cycloalkyloxycarbonyl, mono- to polysubstituted by substituents    independently selected from the group consisting of halogen, cyano,    nitro, hydroxy, mercapto, azido, C₁-C₆alkyl, C₁-C₆haloalkyl,    C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₂-C₇alkoxycarbonyl, formyl, C₂-C₇alkylcarbonyl,    —Si(R₅₁)(R₅₂)(R₅₃) and —Si(OR₅₄)(OR₅₅)(OR₅₆); or-   ah) R₁ and R₂, independently from each other, are the group A-;

wherein A is a three- to ten-membered monocyclic or fused bicyclic ringsystem which can be aromatic, partially saturated or fully saturated andcan contain 1 to 4 hetero atoms selected from the group consisting ofnitrogen, oxygen and sulfur, it not being possible for each ring systemto contain more than 2 oxygen atoms and more than 2 sulfur atoms, and itbeing possible for the three- to ten-membered ring system itself to bemono- or polysubstituted

-   A1) by substituents independently selected from the group consisting    of halogen, cyano, nitro, hydroxy, mercapto, nitro, azido, formyl,    carboxy, —C(═O)—Cl, ═O, ═S, —C(═O)—F, C₁-C₆alkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₅-C₈cycloalkynyl,    C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,    C₃-C₈halocycloalkyl, C₅-C₈halocycloalkenyl, C₅-C₈halocycloalkynyl,    C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy,    C₃-C₆alkynyloxy, C₃-C₈cycloalkyloxy, C₃-C₈halocycloalkyloxy,    C₃-C₈cycloalkenyloxy, C₃-C₈halocycloalkenyloxy, benzyloxy and    phenoxy, where benzyloxy and phenoxy, in turn, may be mono- to    polysubstituted by substituents independently selected from the    group consisting of halogen, cyano, nitro, hydroxy, mercapto, azido,    amino, —SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,    C₁-C₆haloalkoxy, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl and C₁-C₆alkylsulfonyl; or-   A2) by substituents independently selected from the group consisting    of HC(═NOR₅₉)—, (C₁-C₆alkyl)C(═NOR₅₉)—, (C₁-C₆haloalkyl)C(═NOR₅₉)—,    (C₁-C₆alkyl)C(═NOR₅₉)C₁-C₆alkyl- and    (C₁-C₆haloalkyl)C(═NOR₅₉)C₁-C₆alkyl-, wherein R₅₉ is hydrogen,    C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,    C₃-C₆alkynyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, benzyl and    phenyl, and benzyl and phenyl mono- to polysubstituted by halogen,    cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₆alkoxy; or-   A3) by substituents independently selected from the group consisting    of C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, (R₁₄)S(═O)(═NR₁₃)— and (R₁₄)(R₁₅)S(═O)═N—,    wherein R₁₃ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl,    C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₈cycloalkyl,    C₃-C₈halocycloalkyl, phenyl or benzyl, or is phenyl or benzyl mono-    to polysubstituted by halogen, cyano, hydroxy, C₁-C₆alkyl,    C₁-C₆haloalkyl or C₁-C₆alkoxy, and R₁₄ and R₁₅, independently of    each other, are C₁-C₆alkyl, C₃-C₈cycloalkyl, C₁-C₆haloalkyl,    C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl,    benzyl or phenyl, or benzyl or phenyl independently of each other,    substituted by substituents selected from the group consisting of    halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy;    or-   A4) by substituents independently selected from the group consisting    of —NR₅₇R₅₈, —C(═O)NR₅₇R₅₈ and —C(═S)NR₅₇R₅₈; or-   A5) by substituents independently selected from the group consisting    of formyl, C₂-C₇alkylcarbonyl, C₂-C₇haloalkylcarbonyl,    C₃-C₇alkenylcarbonyl, C₃-C₇haloalkenylcarbonyl,    C₄-C₉cycloalkylcarbonyl, C₄-C₉halocycloalkylcarbonyl,    C₂-C₇alkoxycarbonyl, C₂-C₇haloalkoxycarbonyl,    C₃-C₇alkenyloxycarbonyl, C₃-C₇alkynyloxycarbonyl,    C₄-C₉cycloalkoxycarbonyl, C₂-C₇alkylthiocarbonyl and    benzyloxycarbonyl, and benzyloxycarbonyl mono- to polysubstituted by    substituents independently selected from the group consisting of    halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy;    or-   A6) by substituents independently selected from the group consisting    of —Si(R₅₁)(R₅₂)(R₅₃) and —Si(OR₅₄)(OR₅₅)(OR₅₆); or-   A7) by substituents independently selected from the group consisting    of aminosulfinyl, (C₁-C₆alkyl)aminosulfonyl,    N,N-di(C₁-C₆alkyl)aminosulfonyl, di(C₁-C₆alkyl)amino,    (C₁-C₆alkyl)amino, phenyl, phenoxy, benzyl and benzyoxy, where    phenyl, phenoxy, benzyl and benzyloxy for their part may be mono- to    polysubstituted on the phenyl ring by substituents independently    selected form the group consisting of halogen, cyano, hydroxy,    amino, nitro, azido, mercapto, formyl, —SF₅, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl,    C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,    C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio,    C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₆alkylcarbonyl-C₁-C₃alkylthio,    C₂-C₆alkoxycarbonyl-C₁-C₃6alkylthio, cyano-C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylsulfonyl, aminosulfonyl, (C₁-C₆alkyl)aminosulfonyl,    N,N-di(C₁-C₆alkyl)aminosulfonyl, di(C₁-C₆alkyl)amino and    (C₁-C₆alkyl)amino; or-   ai) R₁ and R₂, independently from each other, are —C(═O)NR₅₇R₅₈; or-   aj) R₁ and R₂ together form a C₂-C₆alkylene bridge which may be    mono- to polysubstituted by halogen, cyano, C₁-C₆alkyl or    C₁-C₆haloalkyl groups; or-   ak) R₁ and R₂ together with their interconnecting nitrogen atom are    pyrazolino, pyrazolidino, pyrrolino, imidazolino, imidazolidino,    triazolino, tetrazolino, piperazino, morpholino, thiomorpholino,    each of which, independently of each other, may be mono- to    polysubstituted by methyl groups, halogen, cyano and nitro; or-   al) the fragment

can be

wherein each of the meanings of said fragment can be mono- topolysubstituted by substituents independently selected from the groupconsisting of halogen, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy;

-   ba) R₃, R₄ and R₇, independently from each other, are-   ba1) hydrogen, halogen, cyano, nitro, mercapto, hydroxy, azido,    —SF₅, —NR₆₄R₆₅, wherein R₆₄ and R₆₅, independently of each other,    are hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl,    C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₈cycloalkyl,    C₃-C₈halocycloalkyl, phenyl or benzyl, where phenyl, benzyl for    their part may be mono- to polysubstituted on the phenyl ring by    substituents independently selected form the group consisting of    halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy,    or R₆₄ and R₆₅ together with their interconnecting nitrogen atom are    aziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino,    pyrrolidino, imidazolino, imidazolidino, triazolino, tetrazolino,    piperazino, piperidino, morpholino, thiomorpholino, each of which,    in turn, may be mono- or polysubstituted by substituents selected    from the group consisting of methyl, halogen, cyano and nitro; and    substituents at nitrogen atoms in the ring systems being other than    halogen; or R₃, R₄ and R₇, independently from each other, are    —C(═S)NH₂, —N═C═O, —N═C═S, amino, (R₅₁)(R₅₂)(R₅₃)Si—,    (R₅₁)(R₅₂)(R₅₃)Si—(C₁-C₆alkyl)-, (R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-,    (OR₅₄)(OR₅₅)(OR₅₆)Si— or (OR₂₁₄)(OR₂₁₅)(OR₂₁₆)Si— (C₁-C₆alkyl)-;    wherein R₂₁₄, R₂₁₅ and R₂₁₆ independently of each other, are    halogen, cyano, C₁-C₆alkyl, C₂-C₆alkenyl, C₃-C₈cycloalkyl,    C₅-C₈cycloalkenyl, C₂-C₆alkynyl, benzyl or phenyl; or R₃, R₄ and R₇,    independently from each other, are-   ba2) C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,    aminosulfinyl, aminosulfonyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,    C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkinyloxy,    (C₁-C₆alkyl)aminosulfonyl, di(C₁-C₆alkyl)aminosulfonyl, C₁-C₆alkoxy,    C₂-C₆alkenyloxy, C₂-C₆alkynyloxy, C₁-C₆alkyl-S(═O)(R₁₄)═N—,    (R₁₄)S(═O)(═N—R₁₃)—, (R₁₄)(R₁₅)S(═O)═N—, —S—C₃-C₆-alkenyl,    —S—C₃-C₆-alkynyl, —S—C₃-C₈-cycloalkyl, S-benzyl, or    —S—C₃-C₆-alkenyl, —S—C₃-C₆-alkynyl, —S—C₃-C₈-cycloalkyl or S-benzyl;    all of which can be mono- to polysubstituted by substituents    selected from the group consisting of halogen, cyano, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₁-C₆-alkoxy; or R₃, R₄ and R₇, independently from    each other, are-   ba3) C₁-C₆alkyl, C₂-C₆alkenyl or C₂-C₆alkynyl, or C₁-C₆alkyl,    C₂-C₆alkenyl or C₂-C₆alkynyl mono- to polysubstituted by    substituents independently selected from the group consisting of    halogen, hydroxy, mercapto, cyano, nitro, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆hydroxyalkyl, tri(alkyl)silyl,    C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl and    C₁-C₆haloalkylsulfonyl; or R₃, R₄ and R₇, independently from each    other, are-   ba4) formyl, C₂-C₇alkoxycarbonyl, C₂-C₇haloalkoxycarbonyl,    C₃-C₇alkenyloxycarbonyl, C₃-C₇haloalkenyloxycarbonyl,    C₂-C₇alkylcarbonyl, carboxy, —C(═O)—Cl, —C(═O)—F,    C₂-C₇haloalkylcarbonyl, C₃-C₇alkenylcarbonyl or    C₃-C₇haloalkenylcarbonyl; or R₃, R₄ and R₇, independently from each    other, are-   ba5) phenyl, phenoxy, benzyl or benzyloxy, or phenoxy, benzyl or    benzyloxy mono- to polysubstituted by substituents independently    selected from the group consisting of halogen, cyano, nitro,    hydroxy, mercapto, azido, amino, —SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl,    C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl and    C₁-C₆alkylsulfonyl; or-   bb) R₃, R₄ and R₇, independently of each other, are the groups A-,    A-O— or A-(C₁-C₆alkyl)-, wherein the group A is as defined above    under ah);-   ca) R₅ is hydrogen, C₁-C₁₃alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl,    C₁-C₁₂alkylsulfonyl, C₂-C₁₂alkenylsulfonyl, phenylsulfonyl or    benzylsulfonyl, or is C₁-C₁₂alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl,    C₁-C₁₂alkylsulfonyl, C₂-C₁₂alkenylsulfonyl, phenylsulfonyl or    benzylsulfonyl mono-to polysubstituted by substituents independently    selected from the group consisting of halogen, cyano, nitro,    hydroxy, mercapto, azido, formyl, C₂-C₇alkylcarbonyl,    C₂-C₇haloalkylcarbonyl, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,    C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl and    C₁-C₆alkylsulfonyl; or-   cb1) R₅ is formyl, C₂-C₁₂alkylcarbonyl, C₃-C₁₂alkenylcarbonyl,    C₃-C₁₂alkynylcarbonyl, C₄-C₁₂cycloalkylcarbonyl, benzylcarbonyl,    phenylcarbonyl, C₂-C₁₂alkoxycarbonyl, C₄-C₁₂alkenyloxycarbonyl,    C₄-C₁₂alkynyloxycarbonyl, C₄-C₁₂cycloalkoxycarbonyl,    benzyloxycarbonyl or phenoxycarbonyl, or is-   cb2) C₂-C₁₂alkylcarbonyl, C₃-C₁₂alkenylcarbonyl,    C₃-C₁₂alkynylcarbonyl, C₄-C₁₂cycloalkylcarbonyl, benzylcarbonyl,    phenylcarbonyl, C₂-C₁₂alkoxycarbonyl, C₄-C₁₂alkenyloxycarbonyl,    C₄-C₁₂alkynyloxycarbonyl, C₄-C₁₂cycloalkoxycarbonyl,    benzyloxycarbonyl or phenoxycarbonyl mono- to polysubstituted by    substituents independently selected from the group consisting of    halogen, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or-   cc) R₅ is (R₅₁)(R₅₂)(R₅₃)Si—, (R₅₁)(R₅₂)(R₅₃)Si—(C₁-C₁₂alkyl)-,    (R₅₁)(R₅₂)(R₅₃)Si—(C₃-C₈cycloalkyl)-, (R₅₄O)(R₅₅O)(R₅₆O)Si—,    (R₅₄O)(R₅₅O)(R₅₆O)Si—(C₁-C₁₂alkyl)- or    (R₅₄O)(R₅₅O)(R₅₆O)Si—(C₃-C₈cycloalkyl)-; or-   cd) R₅ is C₁-C₆alkyl-B—C₁-C₁₂alkyl-, C₂-C₆alkenyl-B—C₁-C₁₂alkyl-,    C₂-C₆alkynyl-B—C₁-C₁₂alkyl-, C₃-C₈cycloalkyl-B—C₁-C₁₂alkyl-,    benzyl-B—C₁-C₁₂alkyl-, phenyl-B—C₁-C₁₂alkyl-,    C₁-C₆alkyl-B—C₂-C₁₂alkenyl-, C₂-C₆alkenyl-B—C₂-C₁₂alkenyl-,    C₂-C₆alkynyl-B—C₂-C₁₂alkenyl-, C₃-C₈Cycloalkyl-B—C₂-C₁₂alkenyl-,    benzyl-B—C₂-C₁₂alkenyl-, phenyl-B—C₂-C₁₂alkenyl-,    C₁-C₆alkyl-B—C₂-C₁₂alkynyl-, C₂-C₆alkenyl-B—C₂-C₁₂alkynyl-,    C₂-C₆alkynyl-B—C₂-C₁₂alkynyl-, C₃-C₈cycloalkyl-B—C₂-C₁₂alkynyl-,    benzyl-B—C₂-C₁₂alkynyl-, phenyl-B—C₂-C₁₂alkynyl-,    C₁-C₆alkyl-B—C₃-C₈cycloalkyl-, C₂-C₆alkenyl-B—C₃-C₈cycloalkyl-,    C₂-C₆alkynyl-B—C₃-C₈cycloalkyl-, C₃-C₈cycloalkyl-B—C₃-C₈cycloalkyl-,    benzyl-B—C₃-C₁₂cycloalkyl- or phenyl-B—C₃-C₁₂cycloalkyl-, wherein    the group B is —C(═O)—, —C(═S)—, —C(═NOR₅₉)—, —C(R₆₀)═NO—,    —ON═C(R₆₀)—, —O—C(═O)—, —C(═O)—O—, —O—, —S—, —S(═O)—, —S(═O)₂—,    —S(═O)(═NR₁₃)—, —S(═O)(R₁₄)═N—, —N═S(═O)(R₁₄)—, —N(R₆₂)—C═O)—,    —C═O)—N(R₆₂)—, —N(R₆₂)—SO₂— or —SO₂—N(R₆₂)—;-   cd1) wherein R₆₀ is hydrogen, C₁-C₆alkyl, C₃-C₈cycloalkyl,    C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,    C₂-C₆alkynyl, benzyl or phenyl, or benzyl or phenyl mono- to    polysubstituted by substituents independently selected form the    group consisting of halogen, cyano, hydroxy, C₁-C₆alkyl,    C₁-C₆haloalkyl and C₁-C₆alkoxy, and-   cd2) R₆₂ is hydrogen, C₁-C₆alkyl, C₃-C₈cycloalkyl, C₁-C₆haloalkyl,    C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, benzyl or phenyl,    or benzyl or phenyl mono- to polysubstituted by substituents    independently selected form the group consisting of halogen, cyano,    hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or-   ce) R₅ is C₁-C₆alkyl-B—C₁-C₁₂alkyl-, C₂-C₆alkenyl-B—C₁-C₁₂alkyl-,    C₂-C₆alkynyl-B—C₁-C₁₂alkyl-, C₃-C₈cycloalkyl-B—C₁-C₁₂alkyl-,    benzyl-B—C₁-C₁₂alkyl-, phenyl-B—C₁-C₁₂alkyl-,    C₁-C₆alkyl-B—C₂-C₁₂alkenyl-, C₂-C₆alkenyl-B—C₂-C₁₂alkenyl-,    C₂-C₆alkynyl-B—C₂-C₁₂alkenyl-, C₃-C₈cycloalkyl-B—C₂-C₁₂alkenyl-,    benzyl-B—C₂-C₁₂alkenyl-, phenyl-B—C₂-C₁₂alkenyl-,    C₁-C₆alkyl-B—C₂-C₁₂alkynyl-, C₂-C₆alkenyl-B—C₂-C₁₂alkynyl-,    C₂-C₆alkynyl-B—C₂-C₁₂alkynyl-, C₃-C₈cycloalkyl-B—C₂-C₁₂alkynyl-,    benzyl-B—C₂-C₁₂alkynyl-, phenyl-B—C₂-C₁₂alkynyl-,    C₁-C₆alkyl-B—C₃-C₈cycloalkyl-, C₂-C₆alkenyl-B—C₃-C₈cycloalkyl-,    C₂-C₆alkynyl-B—C₃-C₈cycloalkyl-, C₃-C₈cycloalkyl-B—C₃-C₈cycloalkyl-,    benzyl-B—C₃-C₁₂cycloalkyl-, phenyl-B—C₃-C₁₂cycloalkyl-, all of    which, in turn, are substituted by substituents independently    selected from the group consisting of halogen, cyano, hydroxy,    mercapto, C₁-C₆haloalkyl, C₁-C₆alkoxy, formyl, C₂-C₆alkylcarbonyl,    C₁-C₆alkylthio, C₁-C₆alkylsulfinyl and C₁-C₆alkylsulfonyl; or-   cf) R₅ is A-, A-(C₁-C₆alkyl)-, A-O—(C₁-C₆alkyl)-, A-(C₂-C₆alkenyl)-,    A-O—(C₂-C₆alkenyl)-, A-(C₂-C₆-alkynyl)-, A-O—(C₂-C₆alkynyl)-,    A-(C₃-C₈cycloalkyl)- or A-O—(C₃-C₈cycloalkyl)-; wherein the group A    is as defined above under ah); or-   cg) R₅ signifies the group —N═C(R₈)R₉;-   cg1) wherein R₈ and R₉, independently from each other, are hydrogen,    halogen, cyano, C₁-C₁₂alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkinyl,    C₁-C₁₂alkoxy, formyl, C₂-C₁₂alkylcarbonyl, C₃-C₁₂alkenylcarbonyl,    carboxy, C₂-C₁₂alkoxycarbonyl or C₄-C₁₂alkenyloxycarbonyl, or    C₁-C₁₂alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkinyl, C₁-C₁₂alkoxy,    C₂-C₁₂alkylcarbonyl, C₃-C₁₂alkenylcarbonyl, C₂-C₁₂alkoxycarbonyl or    C₄-C₁₂alkenyloxycarbonyl mono- to polysubstituted by substituents    independently selected from the group consisting of halogen, cyano,    nitro, hydroxy, mercapto, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,    C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl and    C₁-C₆alkylsulfonyl; or-   cg2) R₈ and R₉ together form a C₂-C₈alkylene bridge which may    optionally be mono- to polysubstituted by substituents independently    selected from the group consisting of halogen, cyano, C₁-C₆alkyl and    C₁-C₆haloalkyl; or-   cg3) R₈ and R₉, independently from each other, are the groups A-,    A-O— or A-(C₁-C₆alkyl)-; wherein the group A is as defined above    under ah);-   d) R₆ is hydrogen, halogen, cyano, formyl, C₁-C₆alkyl,    C₁-C₆haloalkyl, —SH, —S—C₁-C₆alkyl, —S—C₁-C₆haloalkyl,    —S—C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl or C₂-C₆alkinyl;    and agronomically acceptable salts/metallic complexes/metalloidic    complexes/isomers/structural    isomers/stereo-isomers/diastereoisomers/enantiomers/tautomers/N-oxides    of those compounds.

Substituents at a nitrogen atom are always different from halogen. Ahydroxy, mercapto or amino substituent is not to be placed on anα-carbon relativ to a heteroatom of a core fragment.

The alkyl groups occurring in the definitions of the substituents can bestraight-chain or branched and are, for example, methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl,hexyl, heptyl and octyl and their branched isomers. Alkoxy, alkenyl andalkynyl radicals are derived from the alkyl radicals mentioned. Thealkenyl and alkynyl groups can be mono- or polyunsaturated.

The cycloalkyl groups occurring in the definitions of the substituentsare, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Halogen is generally fluorine, chlorine, bromine or iodine, preferablyfluorine, bromine or chlorine. This also applies, correspondingly, tohalogen in combination with other meanings, such as haloalkyl orhaloalkoxy.

Haloalkyl groups preferably have a chain length of from 1 to 4 carbonatoms. Halonalkyl is, for example, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl,1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl,difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

Suitable haloalkenyl groups are alkenyl groups which are mono- di- ortrisubstituted by halogen, halogen being fluorine, chlorine, bromine andiodine and in particular fluorine and chlorine, for example2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl,3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and4,4,4-trifluorobut-2-en-1-yl.

Suitable haloalkynyl groups are, for example, alkynyl groups which aremono- or polysubstituted by halogen, halogen being bromine, iodine andin particular fluorine and chlorine, for example 3-fluoropropynyl,3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoro-propynyl and4,4,4-trifluorobut-2-yn-1-yl.

Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy,isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy and ethoxy.Halogenalkoxy is, for example, fluoromethoxy, difluoromethoxy,trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy,2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy andtrifluoromethoxy.

Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl,propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl,isobutoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferablymethoxycarbonyl or ethoxycarbonyl. Haloalkoxy groups preferably have achain length of from 1 to 6 carbon atoms. Haloalkoxy is, for example,fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy,2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferablydifluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groupspreferably have a chain length of from 1 to 6 carbon atoms.

Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl,ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl orisopropoxyethyl.

Alkylthio is, for example, methylthio, ethylthio, propylthio,isopropylthio, n-butylthio, isobutyl-thio, sec-butylthio ortert-butylthio, preferably methylthio and ethylthio. Alkylsulfinyl is,for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl,isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl,tert-butylsulfinyl; preferably methylsulfinyl and ethylsulfinyl.Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl,propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl,sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl orethylsulfonyl.

C₂-C₆alkylcarbonyl is, for example, methylcarbonyl, ethylcarbonyl,propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl,sec-butylcarbonyl, tert-butylcarbonyl or n-pentylcarbonyl and theirbranched isomers, preferably methylcarbonyl and ethylcarbonyl.Haloalkylcarbonyl radicals are derived from the alkyl radicalsmentioned.

In the context of the present invention “mono- to polysubstituted” inthe definition of the substituents, means typically, depending on thechemical structure of the substituents, monosubstituted to seven-timessubstituted, preferably monosubstituted to five-times substituted, morepreferably mono-, double- or triple-substituted.

According to the present invention, a three- to ten-membered monocyclicor fused bicyclic ring system which may be aromatic, partially saturatedor fully saturated is, depending of the number of ring members, forexample, selected from the group consisting of

cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, where saidcycloalkylgroups for their part may be preferably unsubstituted orsubstituted by C₁-C₆alkyl or halogen, or is phenyl, benzyl, naphthyl orthe following heterocyclic groups: pyrrolyl; pyridyl; pyrazolyl;pyrimidyl; pyrazinyl; imidazolyl; thiadiazolyl; quinazolinyl; furyl;oxadiazolyl; indolizinyl; pyranyl; isobenzofuranyl; thienyl;naphthyridinyl; (1-methyl-1H-pyrazol-3-yl)-; (1-ethyl-1H-pyrazol-3-yl)-;(1-propyl-1H-pyrazol-3-yl)-; (1H-pyrazol-3-yl)-;(1,5-dimethyl-1H-pyrazol-3-yl)-; (4-chloro-1-methyl-1H-pyrazol-3-yl)-;(1H-pyrazol-1-yl)-; (3-methyl-1H-pyrazol-1-yl)-;(3,5-dimethyl-1H-pyrazol-1-yl)-; (3-isoxazolyl)-;(5-methyl-3-isoxazolyl)-; (3-methyl-5-isoxazolyl)-; (5-isoxazolyl)-;(1H-pyrrol-2-yl)-; (1-methyl-1H-pyrrol-2-yl)-; (1H-pyrrol-1-yl)-;(1-methyl-1H-pyrrol-3-yl)-; (2-furanyl)-; (5-methyl-2-furanyl)-;(3-furanyl)-; (5-methyl-2-thienyl)-; (2-thienyl)-; (3-thienyl)-;(1-methyl-1H-imidazol-2-yl)-; (1H-imidazol-2-yl)-;(1-methyl-1H-imidazol-4-yl)-; (1-methyl-1H-imidazol-5-yl)-;(4-methyl-2-oxazolyl)-; (5-methyl-2-oxazolyl)-; (2-oxazolyl)-;(2-methyl-5-oxazolyl)-; (2-methyl-4-oxazolyl)-; (4-methyl-2-thiazolyl)-;(5-methyl-2-thiazolyl)-; (2-thiazolyl)-; (2-methyl-5-thiazolyl)-;(2-methyl-4-thiazolyl)-; (3-methyl-4-isothiazolyl)-;(3-methyl-5-isothiazolyl)-; (5-methyl-3-isothiazolyl)-;(1-methyl-1H-1,2,3-triazol-4-yl)-; (2-methyl-2H-1,2,3-triazol-4-yl)-;(4-methyl-2H-1,2,3-triazol-2-yl)-; (1-methyl-1H-1,2,4-triazol-3-yl)-;(1,5-dimethyl-1H-1,2,4-triazol-3-yl)-;(3-methyl-1H-1,2,4-triazol-1-yl)-; (5-methyl-1H-1,2,4-triazol-1-yl)-;(4,5-dimethyl-4H-1,2,4-triazol-3-yl)-;(4-methyl-4H-1,2,4-triazol-3-yl)-; (4H-1,2,4-triazol-4-yl)-;(5-methyl-1,2,3-oxadiazol-4-yl)-; (1,2,3-oxadiazol-4-yl)-;(3-methyl-1,2,4-oxadiazol-5-yl)-; (5-methyl-1,2,4-oxadiazol-3-yl)-;(4-methyl-3-furazanyl)-; (3-furazanyl)-;(5-methyl-1,2,4-oxadiazol-2-yl)-; (5-methyl-1,2,3-thiadiazol-4-yl)-;(1,2,3-thiadiazol-4-yl)-; (3-methyl-1,2,4-thiadiazol-5-yl)-;(5-methyl-1,2,4-thiadiazol-3-yl)-; (4-methyl-1,2,5-thiadiazol-3-yl)-;(5-methyl-1,3,4-thiadiazol-2-yl)-; (1-methyl-1H-tetrazol-5-yl)-;(1H-tetrazol-5-yl)-; (5-methyl-1H-tetrazol-1-yl)-;(2-methyl-2H-tetrazol-5-yl)-; (2-ethyl-2H-tetrazol-5-yl)-;(5-methyl-2H-tetrazol-2-yl)-; (2H-tetrazol-2-yl)-; (2-pyridyl)-;(6-methyl-2-pyridyl)-; (4-pyridyl)-; (3-pyridyl)-;(6-methyl-3-pyridazinyl)-; (5-methyl-3-pyridazinyl)-; (3-pyridazinyl)-;(4,6-dimethyl-2-pyrimidinyl)-; (4-methyl-2-pyrimidinyl)-;(2-pyrimidinyl)-; (2-methyl-4-pyrimidinyl)-; (2-chloro-4-pyrimidinyl)-;(2,6-dimethyl-4-pyrimidinyl)-; (4-pyrimidinyl)-;(2-methyl-5-pyrimidinyl)-; (6-methyl-2-pyrazinyl)-; (2-pyrazinyl)-;(4,6-dimethyl-1,3,5-triazin-2-yl)-; (4,6-dichloro-1,3,5-triazin-2-yl)-;(1,3,5-triazin-2-yl)-; (4-methyl-1,3,5-triazin-2-yl)-;(3-methyl-1,2,4-triazin-5-yl)-; (3-methyl-1,2,4-triazin-6-yl)-;

wherein each R₂₆ is methyl, each R₂₇ and each R₂₈ are independentlyhydrogen, C₁-C₃alkyl, C₁-C₃alkoxy, C₁-C₃alkylthio or trifluoromethyl, X₄is oxygen or sulfur and r=1, 2, 3 or 4.

Where no free valency is indicated in those definitions, for example asin

the linkage site is located at the carbon atom labelled “CH” or in acase such as, for example,

at the bonding site indicated at the bottom left.

Preferred compounds are those, wherein

-   ba) R₃, R₄ and R₇, independently from each other, are-   ba1) hydrogen, halogen, cyano, nitro, mercapto, hydroxy, azido,    —SF₅, —N═C═O, —N═C═S, amino, (R₅₁)(R₅₂)(R₅₃)Si—,    (R₅₁)(R₅₂)(R₅₃)Si—(C₁-C₆alkyl)-, (R₅₁)(R₅₂)(R₅₃)Si— (C₂-C₆alkinyl)-,    (OR₅₄)(OR₅₅)(OR₅₆)Si— or (OR₂₁₄)(OR₂₁₅)(OR₂₁₆)Si—(C₁-C₆alkyl)-    wherein R₂₁₄, R₂₁₅ and R₂₁₆ independently of each other, are    halogen, cyano, C₁-C₆alkyl, C₂-C₆alkenyl, C₃-C₈cycloalkyl,    C₅-C₈cycloalkenyl, C₂-C₆alkynyl, benzyl or phenyl; or R₃, R₄ and R₇,    independently from each other, are-   ba2) C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,    aminosulfinyl, (C₁-C₆alkyl)aminosulfonyl,    di(C₁-C₆alkyl)aminosulfonyl, C₁-C₆alkyl-S(═O)(R₁₄)═N—,    (R₁₄)S(═O)(═N—R₁₃)— or (R₁₄)(R₁₅)S(═O)═N—; or R₃, R₄ and R₇,    independently from each other, are-   ba3) C₁-C₆alkyl, C₂-C₆alkenyl or C₂-C₆alkynyl, or C₁-C₆alkyl,    C₂-C₆alkenyl or C₂-C₆alkynyl mono- to polysubstituted by    substituents independently selected from the group consisting of    halogen, hydroxy, mercapto, cyano, nitro, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆hydroxyalkyl, tri(alkyl)silyl,    C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl and    C₁-C₆haloalkylsulfonyl; or R₃, R₄ and R₇, independently from each    other, are-   ba4) formyl, C₂-C₇alkoxycarbonyl, C₂-C₇haloalkoxycarbonyl,    C₃-C₇alkenyloxycarbonyl, C₃-C₇haloalkenyloxycarbonyl,    C₂-C₇alkylcarbonyl, carboxy, —C(═O)—Cl, —C(═O)—F,    C₂-C₇haloalkylcarbonyl, C₃-C₇alkenylcarbonyl or    C₃-C₇haloalkenylcarbonyl; or R₃, R₄ and R₇, independently from each    other, are-   ba5) phenyl, phenoxy, benzyl or benzyloxy, or phenoxy, benzyl or    benzyloxy mono- to polysubstituted by substituents independently    selected from the group consisting of halogen, cyano, nitro,    hydroxy, mercapto, azido, amino, —SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl,    C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl and    C₁-C₆alkylsulfonyl; or-   bb) R₃, R₄ and R₇, independently of each other, are the groups A-,    A-O— or A-(C₁-C₆alkyl)-, wherein the group A is as defined above    under ah);-   d) R₆ is hydrogen, halogen, cyano, formyl, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl or C₂-C₆alkinyl. and    agronomically acceptable salts/metallic complexes/metalloidic    complexes/isomers/structural    isomers/stereoisomers/diastereoisomers/enantio-mers/tautomers/N-oxides    of those compounds.

In a preferred group of compounds, R₁ and R₂, independently of eachother, are hydrogen, cyano, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, benzyl or C₂-C₇alkylcarbonyl, each of which may be mono-to polysubstituted by substituents independently selected from the groupconsisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio andC₁-C₆alkoxy; or and R₂ together form a C₂-C₆alkylene bridge which may bemono- to polysubstituted by methyl groups; or R₁ and R₂ together withtheir interconnecting nitrogen atom are pyrazolino, pyrazolidino,pyrrolino, imidazolino, imidazolidino, triazolino, tetrazolino,piperazino, morpholino, thiomorpholino, each of which, independently ofeach other, may be mono- to polysubstituted by methyl groups; or

-   R₁ is hydrogen, cyano, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, benzyl or C₂-C₇alkylcarbonyl, each of which may be    mono- to polysubstituted by substituents independently selected from    the group consisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl,    C₁-C₆alkylthio and C₁-C₆alkoxy and R₂ is hydroxy, amino,    C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₈cycloalkyloxy or C₃-C₆alkynyloxy;    or-   R₂ is hydrogen, cyano, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, benzyl or C₂-C₇alkylcarbonyl, each of which may be    mono- to polysubstituted by substituents independently selected from    the group consisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl,    C₁-C₆alkylthio and C₁-C₆alkoxy and R₁ is hydroxy, amino,    C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₈cycloalkyloxy or C₃-C₆alkynyloxy.

Further compounds of formula I are preferred, wherein

-   R₆ is hydrogen, fluoro, chloro, bromo, cyano, C₁-C₆alkyl,    C₁-C₆haloalkyl or CHO;-   R₇ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, halogen or cyano;-   R₄ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇cycloalkyl,    halogen, cyano, hydroxy, C₁-C₆alkoxy, amino, azido, mercapto,    C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, CHO,    C₂-C₇alkylcarbonyl, aziridino, azetidino, pyrazolino, pyrazolidino,    pyrrolino, pyrrolidino, imidazolino, imidazolidino, triazolino,    tetrazolino, piperazino, piperidino, morpholino, thiomorpholino; or    aziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino,    pyrrolidino, imidazolino, imidazolidino, triazolino, tetrazolino,    piperazino, piperidino, morpholino, thiomorpholino, each of which,    in turn, is mono- or polysubstituted by substituents selected from    the group consisting of methyl, halogen; or R₄ is phenyl, or phenyl    which is mono- to polysubstituted by substituents independently    selected from the group consisting of halogen, cyano, hydroxy,    C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy;-   R₃ is hydrogen, C₁-C₆-alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,    C₃-C₇cycloalkyl, halogen, cyano, azido, nitro, —N═C═O, —N═C═S,    —C(═O)NH₂, —C(═S)NH2, —C(═O)NH(CH₃), —C(═S)NH(CH₃), —C(═O)N(CH₃)₂,    —SO₂NH₂, —SO₂NH(CH₃), —SO₂N(CH₃)₂, —C(═S)N(CH₃)₂, —COOH,    tri(C₁-C₄alkyl)silyl, tri-(C₁-C₄alkoxy)silyl, hydroxy, C₁-C₆alkoxy,    amino, azido, mercapto, C₁-C₆alkylamino, C₂-C₁₂dialkylamino,    C₃-C₆alkenylamino, C₆-C₁₂dialkenylamino,    C₁-C₆alkylC₃-C₆alkenylamino, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,    C₁-C₆haloalkylsulfonyl, CHO, C₂-C₇alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₃-C₆alkenyloxycarbonyl,    C₃-C₆alkynyloxycarbonyl, phenyl, aziridino, azetidino, pyrazolino,    pyrazolidino, pyrrolino, pyrrolidino, imidazolino, imidazolidino,    triazolino, tetrazolino, piperazino, piperidino, morpholino or    thiomorpholino; or R₃ is aziridino, azetidino, pyrazolino,    pyrazolidino, pyrrolino, pyrrolidino, imidazolino, imidazolidino,    triazolino, tetrazolino, piperazino, piperidino, morpholino,    thiomorpholino mono- or polysubstituted by substituents    independently selected from the group consisting of methyl, halogen    and phenyl, or by phenyl mono- to polysubstituted by substituents    independently selected from the group consisting of halogen, cyano,    hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or R₃ is    C₁-C₆-alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₇cycloalkyl,    C₁-C₆alkoxy, C₂-C₇alkylcarbonyl, C₂-C₆alkoxycarbonyl,    C₃-C₆alkenyloxycarbonyl, C₃-C₆alkynyloxycarbonyl or phenyl, or is    phenyl mono- to polysubstituted by substituents independently    selected from the group consisting of halogen, cyano, nitro,    C₁-C₆alkyl, C₁-C₆haloalkyl, hydroxy, C₁-C₆alkoxy, C₁-C₆haloakoxy and    phenyl, which phenyl in turn may be mono- to polysubstituted by    substituents independently selected from the group consisting of    halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy;-   R₅ is phenyl, phenyl-C₁-C₁₂alkyl, phenyl-C₃-C₁₂cyclolkyl,    phenyl-C₃-C₁₂alkenyl, or phenyl, phenyl-C₁-C₁₂alkyl,    phenyl-C₃-C₁₂cyclolkyl, phenyl-C₃-C₁₂alkenyl mono- to    polysubstituted by substituents independently selected from the    group consisting of halogen, cyano, nitro, amino, azido, hydroxy,    mercapto, trialkylsilyl, trialkoxysilyl, CHO, COOH, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₃-C₈cycloalkyl,    C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl,    C₂-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,    C₃-C₆haloalkenyloxy, C₃-C₆alkynyloxy, C₃-C₆cycloalkoxy,    C₃-C₆halocycloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,    C₁-C₆haloalkylsulfonyl, —C(═O)NH₂, —C(═S)NH2, —C(═O)NH(CH₃),    —C(═S)NH(CH₃), —C(═O)N(CH₃)₂, —SO₂NH₂, —SO₂NH(CH₃), —SO₂N(CH₃)₂ and    —C(═S)N(CH₃)₂.

Special emphasis should also be given to compounds of formula I wherein

-   R₅ is hydrogen, (R₅₁)(R₅₂)(R₅₃)Si—(C₁-C₁₂alkyl)-,    triC₁-C₆alkylsilyl, phenyl-diC₁-C₆alkylysilyl, C₁-C₁₂alkyl,    C₃-C₁₂alkenyl, C₃-C₁₂alkynyl, C₃-C₁₂cycloalkyl,    C₃-C₁₂cycloalkyl-C₁-C₁₂alkyl, C₅-C₁₂cycloalkenyl,    C₁-C₁₂alkoxy-C₁-C₁₂alkyl, C₁-C₁₂alkenyloxy-C₁-C₁₂alkyl,    C₁-C₁₂alkynyloxy-C₁-C₁₂alkyl, C₁-C₁₂alkylthio-C₁-C₁₂alkyl,    C₁-C₁₂alkylsulfenyl-C₁-C₁₂alkyl, C₁-C₁₂alkylsulfonyl-C₀-C₁₂alkyl,    C₂-C₁₂alkylcarbonyl-C₀-C₁₂alkyl, C₃-C₁₂alkenylcarbonyl-C₀-C₁₂alkyl,    C₂-C₁₂alkoxylcarbonyl-C₀-C₁₂alkyl,    C₃-C₁₂alkenyloxycarbonyl-C₀-C₁₂alkyl or    C₃-C₁₂alkynyloxycarbonyl-C₀-C₁₂alkyl, or R₅ is C₁-C₁₂alkyl,    C₃-C₁₂alkenyl, C₃-C₁₂alkynyl, C₃-C₁₂cycloalkyl,    C₃-C₁₂cycloalkyl-C₁-C₁₂alkyl, C₅-C₁₂cycloalkenyl,    C₁-C₁₂alkoxy-C₁-C₁₂alkyl, C₁-C₁₂alkenyloxy-C₁-C₁₂alkyl,    C₁-C₁₂alkynyloxy-C₁-C₁₂alkyl, C₁-C₁₂alkylthio-C₁-C₁₂alkyl,    C₁-C₁₂alkylsulfenyl-C₁-C₁₂alkyl, C₁-C₁₂alkylsulfonyl-C₀-C₁₂alkyl,    C₂-C₁₂alkylcarbonyl-C₀-C₁₂alkyl, C₃-C₁₂alkenylcarbonyl-C₀-C₁₂alkyl,    C₂-C₁₂alkoxylcarbonyl-C₀-C₁₂alkyl,    C₃-C₁₂alkenyloxycarbonyl-C₀-C₁₂alkyl,    C₃-C₁₂alkynyloxycarbonyl-C₀-C₁₂alkyl mono- to polysubstituted by    substituents independently selected from the group consisting of    halogen, cyano, nitro, amino, hydroxy, mercapto, CHO, COOH,    C₁-C₆-trialkylsilyl, triC₁-C₆alkoxysilyl, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₁-C₆alkenyl,    C₁-C₆haloalkenyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₂-C₇alkylcarbonyl,    C₂-C₇alkoxycarbonyl, C₂-C₇alkenyloxycarbonyl,    C₂-C₇alkynyloxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NH(CH₃),    —C(═S)NH(CH₃), —C(═O)N(CH₃)₂ and —C(═S)N(CH₃)₂. and R₅₁, R₅₂, and    R₅₃ are as defined above.

A further preferred subgroup is represented by the compounds of formulaI wherein

-   R₁ and R₂, independently of each other, are C₁-C₆alkyl,    C₂-C₆alkinyl, hydrogen or pyridine; or R₁ and R₂ together with their    interconnecting nitrogen atom are pyrrolino;-   R₃ is hydrogen, C₁-C₆haloalkyl, C₁-C₆alkyl, halogen, cyano, nitro,    C₁-C₄alkoxy, phenyl, phenyl substituted by halogen,    (R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-, wherein R₅₁, R₅₂ and R₅₃ is as    defined above; especially hydrogen, C₁-C₆alkyl, halogen, cyano,    nitro, C₁-C₄alkoxy, phenyl, phenyl substituted by halogen,    (R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-, wherein R₅₁, R₅₂ and-   R₅₃ is as defined above;-   R₄ is hydrogen, halogen, phenyl, imidazolyl, amino, C₁-C₆alkoxy or    C₁-C₆alkyl;-   R₅ is C₁-C₁₂alkyl or the group A, wherein-   A is a three- to ten-membered monocyclic or fused bicyclic ring    system which can be aromatic, partially saturated or fully saturated    and can contain 1 to 4 hetero atoms selected from the group    consisting of nitrogen, oxygen and sulfur, it not being possible for    each ring system to contain more than 2 oxygen atoms and more than 2    sulfur atoms, and it being possible for the three- to ten-membered    ring system itself to be mono- or polysubstituted by substituents    independently selected from the group consisting of halogen,    C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy and C₁-C₆alkylthio;-   R₆ is hydrogen; and-   R₇ is hydrogen or C₁-C₆alkyl.

In further preferred compounds of formula I, R₆ is —SH, —S—C₁-C₆alkyl or—S—C₁-C₆haloalkyl.

In an outstanding group of compounds of formula I

-   R₁ and R₂, independently of each other, are C₃-C₇cycloalkyl,    C₁-C₆alkyl, C₂-C₆alkinyl, hydrogen or pyridine;-   or R₁ and R₂ together with their interconnecting nitrogen atom are    pyrrolino;-   especially-   R₁ and R₂, independently of each other, are C₁-C₆alkyl,    C₂-C₆alkinyl, hydrogen or pyridine;-   or R₁ and R₂ together with their interconnecting nitrogen atom are    pyrrolino;-   R₃ is hydrogen, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆haloalkyl, halogen,    cyano, phenyl, phenyl substituted by halogen,    (R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-, wherein R₅₁, R₅₂ and R₅₃ is as    defined above;-   especially-   hydrogen, C₁-C₆alkyl, halogen, cyano, phenyl, phenyl substituted by    halogen, (R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-, wherein R₅₁, R₅₂ and R₅₃    is as defined above;-   R₄ is hydrogen, halogen, C₁-C₆alkoxy or C₁-C₆alkyl;-   especially-   hydrogen or C₁-C₆alkyl;-   R₅ is C₁-C₆alkyl, phenyl or pyridyl or C₁-C₆alkyl, phenyl or pyridyl    mono- or disubstituted by halogen, C₁-C₆alkyl, C₁-C₆haloalkyl,    C₁-C₆alkoxy, C₁-C₆alkylthio,-   especially-   C₁-C₆alkyl, phenyl or pyridyl or phenyl or pyridyl mono- or    disubstituted by halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,    C₁-C₆alkylthio,-   R₆ is hydrogen; and-   R₇ is hydrogen or C₁-C₆alkyl. Further preferred embodiments of the    present invention are the embodiments E1 to E151, which are defined    as compounds of formula I which are represented by one formula    selected from the group consisting of the formulae T1 to T151 as    described below,-   wherein in formulae T1 to T151 the meanings of the substituents R₁,    R₂, R₅ and R₆ have the preferred meanings as mentioned above.

For example, embodiment E1 is represented by the compounds of formula T1

wherein

-   R₁ and R₂, independently of each other, are hydrogen, cyano,    C₁-C₆alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, benzyl or    C₂-C₇alkylcarbonyl, each of which may be mono- to polysubstituted by    substituents independently selected from the group consisting of    halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio and C₁-C₆alkoxy;    or R₁ and R₂ together form a C₂-C₆alkylene bridge which may be mono-    to polysubstituted by methyl groups; or R₁ and R₂ together with    their interconnecting nitrogen atom are pyrazolino, pyrazolidino,    pyrrolino, imidazolino, imidazolidino, triazolino, tetrazolino,    piperazino, morpholino, thiomorpholino, each of which, independently    of each other, may be mono- to polysubstituted by methyl groups; or-   R₁ is hydrogen, cyano, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, benzyl or C₂-C₇alkylcarbonyl, each of which may be    mono- to polysubstituted by substituents independently selected from    the group consisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl,    C₁-C₆alkylthio and C₁-C₆alkoxy and R₂ is hydroxy, amino,    C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₈cycloalkyloxy or C₃-C₆alkynyloxy;    or R₂ is hydrogen, cyano, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, benzyl or C₂-C₇alkylcarbonyl, each of which may be    mono- to polysubstituted by substituents independently selected from    the group consisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl,    C₁-C₆alkylthio and C₁-C₆alkoxy and R₁ is hydroxy, amino,    C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₈cycloalkyloxy or C₃-C₆alkynyloxy;-   R₆ is hydrogen, fluoro, chloro, bromo, cyano, C₁-C₆alkyl,    C₁-C₆haloalkyl or CHO; and-   R₅ is phenyl, phenyl-C₁-C₁₂alkyl, phenyl-C₃-C₁₂cyclolkyl,    phenyl-C₃-C₁₂alkenyl, or phenyl, phenyl-C₁-C₁₂alkyl,    phenyl-C₃-C₁₂cyclolkyl, phenyl-C₃-C₁₂alkenyl mono- to    polysubstituted by substituents independently selected from the    group consisting of halogen, cyano, nitro, amino, azido, hydroxy,    mercapto, trialkylsilyl, trialkoxysilyl, CHO, COOH, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₃-C₈cycloalkyl,    C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl,    C₂-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,    C₃-C₆haloalkenyloxy, C₃-C₆alkynyloxy, C₃-C₆cycloalkoxy,    C₃-C₆halocycloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,    C₁-C₆haloalkylsulfonyl, —C(═O)NH₂, —C(═S)NH2, —C(═O)NH(CH₃),    —C(═S)NH(CH₃), —C(═O)N(CH₃)₂, —SO₂NH₂, —SO₂NH(CH₃), —SO₂N(CH₃)₂ and    —C(═S)N(CH₃)₂.

Special emphasis should also be given to compounds of embodiment E1wherein

-   R₅ is hydrogen, triC₁-C₆alkylsilyl, phenyl-diC₁-C₆alkylysilyl,    C₁-C₁₂alkyl, C₃-C₁₂alkenyl, C₃-C₁₂alkynyl, C₃-C₁₂cycloalkyl,    C₃-C₁₂cycloalkyl-C₁-C₁₂alkyl, C₆-C₁₂cycloalkenyl,    C₁-C₁₂alkoxy-C₁-C₁₂alkyl, C₁-C₁₂alkenyloxy-C₁-C₁₂alkyl,    C₁-C₁₂alkynyloxy-C₁-C₁₂alkyl, C₁-C₁₂alkylthio-C₁-C₁₂alkyl,    C₁-C₁₂alkylsulfenyl-C₁-C₁₂alkyl, C₁-C₁₂alkylsulfonyl-C₀-C₁₂alkyl,    C₂-C₁₂alkylcarbonyl-O₀-C₁₂alkyl, C₃-C₁₂alkenylcarbonyl-C₀-C₁₂alkyl,    C₂-C₁₂alkoxylcarbonyl-C₀-C₁₂alkyl,    C₃-C₁₂alkenyloxycarbonyl-C₀-C₁₂alkyl or    C₃-C₁₂alkynyloxycarbonyl-C₀-C₁₂alkyl, or R₅ is C₁-C₁₂alkyl,    C₃-C₁₂alkenyl, C₃-C₁₂alkynyl, C₃-C₁₂cycloalkyl,    C₃-C₁₂cycloalkyl-C₁-C₁₂alkyl, C₆-C₁₂cycloalkenyl,    C₁-C₁₂alkoxy-C₁-C₁₂alkyl, C₁-C₁₂alkenyloxy-C₁-C₁₂alkyl,    C₁-C₁₂alkynyloxy-C₁-C₁₂alkyl, C₁-C₁₂alkylthio-C₁-C₁₂alkyl,    C₁-C₁₂alkylsulfenyl-C₁-C₁₂alkyl, C₁-C₁₂alkylsulfonyl-C₀-C₁₂alkyl,    C₂-C₁₂alkylcarbonyl-C₀-C₁₂alkyl, C₃-C₁₂alkenylcarbonyl-C₀-C₁₂alkyl,    C₂-C₁₂alkoxylcarbonyl-C₀-C₁₂alkyl,    C₃-C₁₂alkenyloxycarbonyl-C₀-C₁₂alkyl,    C₃-C₁₂alkynyloxycarbonyl-C₀-C₁₂alkyl mono- to polysubstituted by    substituents independently selected from the group consisting of    halogen, cyano, nitro, amino, hydroxy, mercapto, CHO, COOH,    C₁-C₆-trialkylsilyl, triC₁-C₆alkoxysilyl, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₁-C₆alkenyl,    C₁-C₆haloalkenyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₂-C₇alkylcarbonyl,    C₂-C₇alkoxycarbonyl, C₂-C₇alkenyloxycarbonyl,    C₂-C₇alkynyloxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NH(CH₃),    —C(═S)NH(CH₃), —C(═O)N(CH₃)₂ and —C(═S)N(CH₃)₂.

In further preferred group of compounds of embodiment E1, R₆ is —SH,—S—C₁-C₆alkyl or —S—C₁-C₆haloalkyl.

In an outstanding group of compounds of embodiment E1,

-   R₁ and R₂, independently of each other, are C₁-C₆alkyl,    C₂-C₆alkinyl, hydrogen or pyridine;-   or R₁ and R₂ together with their interconnecting nitrogen atom are    pyrrolino;-   R₅ is C₁-C₆alkyl, phenyl or pyridyl or phenyl or pyridyl mono- or    disubstituted by substituents selected from the group consisting of    halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy and C₁-C₆alkylthio;    and R₆ is hydrogen. The substituents R₁, R₂, R₅ and R₆ of the    embodiments E2 to E151 are defined accordingly.

Compounds of formula I as well as intermediates and reagents used can beprepared by methods known to a skilled chemist in a variety of ways, orthey are commercially available.

Compounds of formula I can be prepared by a number of known methods fromamino compounds of formula II. Such methods include the following:

-   a) Scheme 1 below: An amide of formula (R₆)C(═O)—N(R₁)(R₂), or a    formamide of formula HC(═O)—N(R₁)(R₂), is treated with reagents like    POCl₃, PCl₃, SOCl₂, COCl₂, Ph—SO₂Cl, Me₂N—SO₂Cl, (CF₃CO)₂O and then    with an amino compound of formula II.-   b) Scheme 1 below: Reacting the amino derivative of formula II,    wherein R₃, R₄, R₅ and R₇ is as defined under formula I above, with    a compound of formula R₆—C(OR)₂—N(R₁)(R₂), wherein R₁, R₂ and R₆ is    as defined under formula I above, or with a compound of formula    R₆—C(OR)(NR₁R₂)₂, wherein R is preferably an alkyl or phenyl group    and R₁, R₂ and R₆ is as defined under formula I above, or, for the    former reagent, the two R together form an alkylidene fragment. Such    transformations are described in the literature, e.g. in:    Bashkirskii Khimicheskii Zhurnal (2000), 7 (2), 5-9; Indian Journal    of Chemistry, Section B: Organic Chemistry Including Medicinal    Chemistry (1981), 20B(12), 1075-7; ARKIVOC (Gainesville, Fla.,    United States) (2004), (10), 20-38.

-   c) Scheme 2 below: An amino derivative of formula II can be    converted into an amide and this, in turn, into the final compound    of formula I by a two step sequence: 1) activation (using e.g. PCl₅    or Ph₃PO together with (CF₃SO₂)₂O, followed 2) by the reaction with    a amine of formula HN(R₁)(R₂), wherein R₁ and R₂ is as defined under    formula I above. Such methods are describe in the literature, e.g.    in Journal of Organic Chemistry (1989), 54 (5), 1144-9; Zhurnal    Organicheskoi Khimii (1989), 25 (2), 357-67.

-   d) Scheme 3 below: An amino derivative of formula II can first be    transformed into the corresponding isocyanate. This one, in turn, is    then reacted with a formamide of general formula HC(═O)—N(R₁)(R₂),    wherein R₁ and R₂ is as defined under formula I above, to obtain a    formamidine of formula I. Such methods are to be found in the    literature, e.g. in Journal of Pharmaceutical Sciences (1964), 53    (12), 1539-40; Journal für Praktische Chemie (Leipzig) (1961), 13,    265-71.

-   e) Scheme 4 below: Compounds of general formulas (I_(e2)) and    (I_(e1)) are subsets of compounds described by general formula (I).    Compounds of general formula (I_(e2)) can be obtained by reacting a    compound of general formula (I_(e1)) with an amine of formula    HN(R_(1e))(R_(2e)) under appropriate conditions. Fragments of the    formula —N(R_(1e1))(R_(2e1)) are a subset of fragments of the    formula —N(R₁)(R₂), and compounds of the formula    HN(R_(1e2))(R_(2e2)) form a subset of compounds of formula HNR₁R₂.    Such procedures can be found in the literature, e.g. in Tetrahedron    Letters (1989), 30 (1), 47-50; Khimicheskii Zhurnal (2000), 7 (2),    5-9.

-   f) Scheme 5 below: Compounds of general formula I_(f), being a    subset of compounds of formula I, may be prepared by acylating or    alkylating compounds of formula I_(f1). Such protocols are to be    found in the literature, e.g. in Chemical & Pharmaceutical Bulletin    (1983), 31 (10), 3534-43; Zhurnal Organicheskoi Khimii (1989), 25    (2), 357-67; Tetrahedron (2000), 56 (39), 7811-7816; Journal of the    Chemical Society, Transactions (1923), 123, 3359-75.

Substituents of formulas R and R_(f) are subsets of substituents offormula R₁ (or R₂).

Compounds of formula II may be prepared from the corresponding nitroderivatives of formula III by a variety of reduction procedures.

-   g) Scheme 6 below: The reduction methods include transformation of    the nitro compound of formula III, wherein R₃, R₄, R₅ and R₇ is as    defined under formula I above, in the presence of a catalyst, e.g.    Pd-, Ni- or Pt-based catalysts, and molecular hydrogen, in a    suitable solvent at ambient temperature or at elevated temperatures,    at normal or at a higher pressure, or the reduction may be carried    out by one of several metal reduction methods, e.g. using metals    such as Fe, Sn, Zn or reagents such as SnCl₂ in an acidic and/or    protic medium.

Nitro compounds of formula III may be prepared in a number of ways.These include the following:

-   h) Scheme 7 below: Compounds of formula III can be obtained from    compounds ofl formula IV, wherein R₃, R₄ and R₇ are as defined under    formula I above, having a leaving group R₁₀₀, where R₁₀₀ is SH—,    nitro, halogen, imidazolyl, triazolyl, C₁-C₆alkylthio,    C₁-C₆alkylsulfenyl or C₁-C₆alkysulfonyl, preferably halogen,    C₁-C₆alkylthio, C₁-C₆alkylsulfenyl, C₁-C₆alkylsulfonyl, in    particular F, Cl, Br, I, MeS—, MeSO— or MeSO₂—; or R₁₀₀ is    imidazolyl, triazolyl, PhSO₂—, CF₃SO₂—O—, p-MeC₆H₄SO₂O—, O₂N—) by    reaction with R₅—OH, wherein R₅ is as defined under formula I above,    in the presence of a base. This conversion may be effected by using    a preformed salt of R₅OH.

-   i) Scheme 8 below: Compounds of formula III, may be obtained by    reacting a precursor of formula IV_(i) either with an electrophilic    precursor R_(5i)—X, R_(5i) being a being a suitable subset of R₅ and    X being a leaving group such as a halogen or MeSO₂O or p-MeC₆H₄SO₂O,    the reaction conducted preferentially in the presence of a base. Or,    alternatively, compound IV, can be reacted with an alcohol of    formula R₅, —OH under Mitsunobu conditions, using e.g. Ph₃P,    EtO-C—N═N—CO-OEt in solvents such as dioxane, THF or toluene. Such    methods are described in the literature, e.g. in Journal of    Medicinal Chemistry (2006), 49 (15), 4455-4458; Tetrahedron Letters    (2006), 47 (28), 4897-4901.

-   j) Scheme 9 below: Nitro compounds of formula III_(j), being a    subset of compounds of formula III, can also be obtained by using a    suitable precursor V_(j) with a group Y, e.g. a halogen or a group    CF₃SO₂O, that can be used to introduce R_(3j), R_(3j) being a subset    of R₃. For such transformations a large number of methods are firmly    established and described in the literature (e.g. Suzuki,    Suzuki-Miyaura, Negishi, Stille coupling reactions, or Heck and    Sonogashira reactions).

-   k) Scheme 10 below: Compounds of formula III_(k), being a subset of    compounds described by formula III, may be obtained as described in    scheme 10 by using well-established methods. This includes e.g.    Suzuki-Miyaura and Stille coupling reactions using the electrophilic    species (R_(3k1))—X, X being a leaving group, in particular Cl, Br    or I. Within the definition given in scheme 10, R_(3k1) is part of    the many molecular scaffolds that are commonly used for the    reactions possible here. (R_(3k1))—X includes aryl-, hetaryl- or    vinyl-based halides. The method described here includes also    reactions with a precursor (R_(5k2))—H, forming a nucleophilic    species under appropriate conditions to be attached to the pyridine    core fragment of (V_(k)). Among the latter cases are e.g. amination    reactions or reactions with a precursor carbonyl compound    (displaying CH acidity    to the carbonyl). In both cases, there are many catalytic systems    described in the literature to effect transformation.

-   l) Scheme 11 below: Compounds of formula III_(L), being a subset of    compounds of formula III, may be obtained by the reaction of    electrophilic compounds of formula (R_(3La))—X (X being a leaving    group, such as a halogen or MeSO₂O) with the anion generated from    compounds of formula V_(L) with a base under suitable conditions, as    is well-described in the literature.

-   m) Scheme 12 below: Compounds of formula III_(m), being a subset of    compounds of formula III, can also be prepared by transforming a    precursor functional group R_(3m1) into the group R_(3m). Fragments    of formula R_(3m), being a subset of the fragments defined by the    formula R₃, and the precursor fragment of formula R_(3ma) being such    that the definitions of formula R_(3m) are valid after the    transformation has been carried out. By way of example: (R_(3m1))—    can be HCO— that can be converted into F₂CH— using reagents such as    DAST or SF₄, or (R_(3m1)—) can be H₃C—H₂C—S— that can be transformed    into H₃C—H₂C—S(═O)— and H₃C—H₂C—S(═O)₂— oxidatively using standard    methods that are well-described in the literature; or (R_(3m1)—) can    be —C═S)NH₂ that can be transformed into a optionally substituted    thiazolyl fragment using standard methods as described in the    literature.

-   n) The methods introduced above—under j) to m)—dealing with the    introduction and transformation of the substituent R₃, can also be    applied in the cases of the substituents R₄ and R₇.-   o) Scheme 13 below: The methods mentioned above under j) to m) are    also applicable, in a proper form, for the elaboration of compounds    of formula III_(o), describing compounds of a subset of compounds of    the formula III. In this case, a suitable substituent R_(5o1), is    transformed into a substituent R_(5o), substituents R_(5o) being a    subset of substituent R₅.

-   p) Scheme 14 below: The methods as described above under chapters g)    to o) are also valid for the cases, where the nitro group is    replaced by a hydrogen or by a amino group, or by a suitably    protected amino group (such as are e.g. —NH—C(═O)—CH₃,    —NH—C(═O)-tert-butyl, —NH-benzoyl, —N(C(═O)—CH₃)₂, -phthaloyl,    —N(benzyl)₂, —NH—C(═O)—O-tert-butyl), or by some amidine group    —N═C(R₆)—N(R₁)(R₂). One skilled in the art knows, however, that this    is not a general principle, but applies to cases with compatible    functional groups. By way of example, this scenario is shown in    scheme 14 for the transformations described in chapter m) above for    the case where an amidine group is present instead of the nitro    function (formula X). Cf. definitions of R_(3m1) and R_(3m) in    chapter m) above and R₁₀₀ is as defined in chapter h) above. The    compounds of formula X wherein R₁, R₂, R₃, R₄, R₆ and R₇ are as    defined under formula I in claim I and R₁₀₀ is SH—, nitro, halogen,    imidazolyl, triazolyl, C₁-C₆alkylthio, C₁-C₆alkylsulfenyl or    C₁-C₆alkysulfonyl are novel and therefore represent a further object    of the present invention.

-   q) Scheme 15 below: Compounds of the formula III can be prepared by    direct nitration of a suitable precursor, provided the nitration    protocol in question is compatible with the starting material. This    nitration can be carried out in a number of well-established ways.    E.g. using the mixed acid system of HNO₃ and H₂SO₄. Along these    lines, the precursor VI may be dissolved first in H₂SO₄ and reacted    with the mixed acid system, or it may be treated directly with the    mixed acid system under a variety of conditions. In addition, the    nitration may be carried out in an inert solvent system, using    nitrating agents such as BF₄NO₄. Nitration may also be carried out    using HNO₃ in an appropriate solvent such as H₂O, AcOH, acetic acid    anhydride. The same methods may also be applied to a suitable    precursor of formula VII to give a compound of formula IV. X is a    leaving group as defined in chapter h) above.

-   r) Scheme16 below: Compounds of formula VII can be synthesized by a    number of well-established methods. In particular by transforming a    precursors of formulae VIII or IX. X is a leaving group as defined    in chapter h) above.-   r1) If a compound of formula VIII is the precursor the methods    include the transformation to a compound where X is Cl, with    reagents such as PCl₅, POCl₃, SOCl₂ or ClCO—COCl normally under    heating in an inert solvent, either without or in the presence of a    suitable base. If X is Br, the preferred reagents include POBr₃,    PBr₃ and NBS together with Ph₃P. If X is CF₃SO₂O, preferred    preparative methods use reagents such as (CF₃SO₂)₂O in the presence    of a base, e.g. Et₃N or 2,6-lutidine.-   r2) If a compound of formula (IX) is the precursor, preferred    procedures include the following. If X is equal to Cl or Br, a    Sandmeyer-type protocol can be used, i.e. diazotization followed by    reaction with cuprous chloride or bromide. Or, X is F, in which    case, after diazotization, a diazonium fluoroborate salt is produced    that is then converted to the fluoro derivative. The fluoroborate    may also be produced with an organic nitrite and BF₃-etherate.

-   s) Scheme 17 below: A large number of compounds of formulae VIII and    IX or of compounds being potential precursors thereof are    commercially available. In addition, there are many ways of    achieving the syntheses of pyridine building blocks of general    formulae VIII and 1× as is amply documented in the literature. By    way of example, we mention the following 3 syntheses within the    general definition of compounds of formula IX in schemes 18 to 20    below.

Journal of Organic Chemistry (2005), 70 (4), 1364-1368

Journal of Heterocyclic Chemistry (1977), 14 (2), 203-5

Synthesis (2005), (8), 1269-1278

The reactions leading to compounds of formula I are advantageouslycarried out in aprotic inert organic solvents. Such solvents arehydrocarbons such as benzene, toluene, xylene or cyclohexane,chlorinated hydrocarbons such as dichloromethane, trichloromethane,tetrachloromethane or chlorobenzene, ethers such as diethyl ether,ethylene glycol dimethyl ether, diethylene glycol dimethyl ether,tetrahydrofuran or dioxane, nitriles such as acetonitrile orpropionitrile, amides such as N,N-dimethylformamide, diethylformamide orN-methylpyrrolidinone. The reaction temperatures are advantageouslybetween −20° C. and +120° C. In general, the reactions are slightlyexothermic and, as a rule, they can be carried out at room temperature.To shorten the reaction time, or else to start the reaction, the mixturemay be heated briefly to the boiling point of the reaction mixture. Thereaction times can also be shortened by adding a few drops of base asreaction catalyst. Suitable bases are, in particular, tertiary aminessuch as trimethylamine, triethylamine, quinuclidine,1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or1,5-diazabicyclo-[5.4.0]undec-7-ene. However, inorganic bases such ashydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g.sodium hydroxide or potassium hydroxide, carbonates such as sodiumcarbonate and potassium carbonate, or hydrogen carbonates such aspotassium hydrogen carbonate and sodium hydrogen carbonate may also beused as bases. The bases can be used as such or else with catalyticamounts of a phase-transfer catalyst, for example a crown ether, inparticular 18-crown-6, or a tetraalkylammonium salt.

The compounds of formula I can be isolated in the customary manner byconcentrating and/or by evaporating the solvent and purified byrecrystallization or trituration of the solid residue in solvents inwhich they are not readily soluble, such as ethers, aromatichydrocarbons or chlorinated hydrocarbons.

The compounds of formula I and, where appropriate, the tautomersthereof, can be present in the form of one of the isomers which arepossible or as a mixture of these, for example in the form of pureisomers, such as antipodes and/or diastereomers, or as isomer mixtures,such as structural isomer, stereo isomer, diastereoisomer and enantiomermixtures, for example racemates, diastereomer mixtures or racematemixtures, depending on the number, absolute and relative configurationof asymmetric carbon atoms which occur in the molecule and/or dependingon the configuration of non-aromatic double bonds which occur in themolecule; the invention relates to the pure isomers and also to allisomer mixtures which are possible and is to be understood in each casein this sense hereinabove and hereinbelow, even when stereochemicaldetails are not mentioned specifically in each case.

Diastereo-isomeric mixtures or racemate mixtures of compounds I, whichcan be obtained depending on which starting materials and procedureshave been chosen can be separated in a known manner into the purediasteromers or racemates on the basis of the physicochemicaldifferences of the components, for example by fractionalcrystallization, distillation and/or chromatography.

Enantiomeric mixtures, such as racemates, which can be obtained in asimilar manner can be resolved into the optical antipodes by knownmethods, for example by recrystallization from an optically activesolvent, by chromatography on chiral adsorbents, for examplehigh-performance liquid chromatography (HPLC) on acetyl celulose, withthe aid of suitable microorganisms, by cleavage with specific,immobilized enzymes, via the formation of inclusion compounds, forexample using chiral crown ethers, where only one enantiomer iscomplexed, or by conversion into diastereomeric salts, for example byreacting a basic end-product racemate with an optically active acid,such as a carboxylic acid, for example camphor, tartaric or malic acid,or sulfonic acid, for example camphorsulfonic acid, and separating thediastereomer mixture which can be obtained in this manner, for exampleby fractional crystallization based on their differing solubilities, togive the diastereomers, from which the desired enantiomer can be setfree by the action of suitable agents, for example basic agents.

Pure diastereomers or enantiomers can be obtained according to theinvention not only by separating suitable isomer mixtures, but also bygenerally known methods of diastereoselective or enantioselectivesynthesis, for example by carrying out the process according to theinvention with starting materials of a suitable stereochemistry.

It is advantageous to isolate or synthesize in each case thebiologically more effective isomer, for example enantiomer ordiastereomer, or isomer mixture, for example enantiomer mixture ordiastereomer mixture, if the individual components have a differentbiological activity.

The compounds I and, where appropriate, the tautomers thereof, can, ifappropriate, also be obtained in the form of hydrates and/or includeother solvents, for example those which may have been used for thecrystallization of compounds which are present in solid form.

It has now been found that the compounds of formula I according to theinvention have, for practical purposes, a very advantageous spectrum ofactivities for protecting useful plants against diseases that are causedby phytopathogenic microorganisms, such as fungi, bacteria or viruses.

The invention relates to a method of controlling or preventinginfestation of useful plants by phytopathogenic microorganisms, whereina compound of formula I is applied as active ingredient to the plants,to parts thereof or the locus thereof. The compounds of formula Iaccording to the invention are distinguished by excellent activity atlow rates of application, by being well tolerated by plants and by beingenvironmentally safe. They have very useful curative, preventive andsystemic properties and are used for protecting numerous useful plants.The compounds of formula I can be used to inhibit or destroy thediseases that occur on plants or parts of plants (fruit, blossoms,leaves, stems, tubers, roots) of different crops of useful plants, whileat the same time protecting also those parts of the plants that growlater e.g. from phytopathogenic microorganisms.

It is also possible to use compounds of formula I as dressing agents forthe treatment of plant propagation material, in particular of seeds(fruit, tubers, grains) and plant cuttings (e.g. rice), for theprotection against fungal infections as well as against phytopathogenicfungi occurring in the soil.

Furthermore the compounds of formula I according to the invention may beused for controlling fungi in related areas, for example in theprotection of technical materials, including wood and wood relatedtechnical products, in food storage or in hygiene management.

The compounds of formula I are, for example, effective against thephytopathogenic fungi of the following classes: Fungi imperfecti (e.g.Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercosporaand Alternaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia,Puccinia). Additionally, they are also effective against the Ascomycetesclasses (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula)and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara).Outstanding activity has been observed against powdery mildew (Erysiphespp.). Furthermore, the novel compounds of formula I are effectiveagainst phytopathogenic bacteria and viruses (e.g. against Xanthomonasspp, Pseudomonas spp, Erwinia amylovora as well as against the tobaccomosaic virus). Good activity has been observed against Asian soybeanrust (Phakopsora pachyrhizi).

Within the scope of the invention, useful plants to be protectedtypically comprise the following species of plants: cereal (wheat,barley, rye, oat, rice, maize, sorghum and related species); beet (sugarbeet and fodder beet); pomes, drupes and soft fruit (apples, pears,plums, peaches, almonds, cherries, strawberries, raspberries andblackberries); leguminous plants (beans, lentils, peas, soybeans); oilplants (rape, mustard, poppy, olives, sunflowers, coconut, castor oilplants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers,melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges,lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus,cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae(avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee,eggplants, sugar cane, tea, pepper, vines, hops, bananas and naturalrubber plants, as well as ornamentals.

The term “useful plants” is to be understood as including also usefulplants that have been rendered tolerant to herbicides like bromoxynil orclasses of herbicides (such as, for example, HPPD inhibitors, ALSinhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron,EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors) as a result of conventional methodsof breeding or genetic engineering. An example of a crop that has beenrendered tolerant to imidazolinones, e.g. imazamox, by conventionalmethods of breeding (mutagenesis) is Clearfield® summer rape (Canola).Examples of crops that have been rendered tolerant to herbicides orclasses of herbicides by genetic engineering methods include glyphosate-and glufosinate-resistant maize varieties commercially available underthe trade names RoundupReady® and LibertyLink®.

The term “useful plants” is to be understood as including also usefulplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising one or more selectivelyacting toxins, such as are known, for example, from toxin-producingbacteria, especially those of the genus Bacillus.

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a CryIA(b) toxin); YieldGardRootworm® (maize variety that expresses a CryIIIB(b1) toxin); YieldGardPlus® (maize variety that expresses a CryIA(b) and a CryIIIB(b1) toxin);Starlink® (maize variety that expresses a Cry9 (c) toxin); Herculex I®(maize variety that expresses a CryIF(a2) toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a CryIA(c) toxin); Bollgard I® (cotton variety that expressesa CryIA(c) toxin); Bollgard II® (cotton variety that expresses aCryIA(c) and a CryIIA(b) toxin); VIPCOT® (cotton variety that expressesa VIP toxin); NewLeaf® (potato variety that expresses a CryIIIA toxin);Nature-Gard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

The term “useful plants” is to be understood as including also usefulplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising antipathogenicsubstances having a selective action, such as, for example, theso-called “pathogenesis-related proteins” (PRPs, see e.g. EP-A-0 392225). Examples of such antipathogenic substances and transgenic plantscapable of synthesising such antipathogenic substances are known, forexample, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191. Themethods of producing such transgenic plants are generally known to theperson skilled in the art and are described, for example, in thepublications mentioned above.

The term “locus” of a useful plant as used herein is intended to embracethe place on which the useful plants are growing, where the plantpropagation materials of the useful plants are sown or where the plantpropagation materials of the useful plants will be placed into the soil.An example for such a locus is a field, on which crop plants aregrowing.

The term “plant propagation material” is understood to denote generativeparts of the plant, such as seeds, which can be used for themultiplication of the latter, and vegetative material, such as cuttingsor tubers, for example potatoes. There may be mentioned for exampleseeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes andparts of plants. Germinated plants and young plants which are to betransplanted after germination or after emergence from the soil, mayalso be mentioned. These young plants may be protected beforetransplantation by a total or partial treatment by immersion. Preferably“plant propagation material” is understood to denote seeds.

The compounds of formula I can be used in unmodified form or,preferably, together with carriers and adjuvants conventionally employedin the art of formulation.

Therefore the invention also relates to compositions for controlling andprotecting against phytopathogenic microorganisms, comprising a compoundof formula I and an inert carrier, and to a method of controlling orpreventing infestation of useful plants by phytopathogenicmicroorganisms, wherein a composition, comprising a compound of formulaI as active ingredient and an inert carrier, is applied to the plants,to parts thereof or the locus thereof.

To this end compounds of formula I and inert carriers are convenientlyformulated in known manner to emulsifiable concentrates, coatablepastes, directly sprayable or dilutable solutions, dilute emulsions,wettable powders, soluble powders, dusts, granulates, and alsoencapsulations e.g. in polymeric substances. As with the type of thecompositions, the methods of application, such as spraying, atomising,dusting, scattering, coating or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances. Thecompositions may also contain further adjuvants such as stabilizers,antifoams, viscosity regulators, binders or tackifiers as well asfertilizers, micronutrient donors or other formulations for obtainingspecial effects.

Suitable carriers and adjuvants can be solid or liquid and aresubstances useful in formulation technology, e.g. natural or regeneratedmineral substances, solvents, dispersants, wetting agents, tackifiers,thickeners, binders or fertilizers. Such carriers are for exampledescribed in WO 97/33890.

The compounds of formula I or compositions, comprising a compound offormula I as active ingredient and an inert carrier, can be applied tothe locus of the plant or plant to be treated, simultaneously or insuccession with further compounds. These further compounds can be e.g.fertilizers or micronutrient donors or other preparations whichinfluence the growth of plants. They can also be selective herbicides aswell as insecticides, fungicides, bactericides, nematicides,molluscicides or mixtures of several of these preparations, if desiredtogether with further carriers, surfactants or application promotingadjuvants customarily employed in the art of formulation.

A preferred method of applying a compound of formula I, or acomposition, comprising a compound of formula I as active ingredient andan inert carrier, is foliar application. The frequency of applicationand the rate of application will depend on the risk of infestation bythe corresponding pathogen. However, the compounds of formula I can alsopenetrate the plant through the roots via the soil (systemic action) bydrenching the locus of the plant with a liquid formulation, or byapplying the compounds in solid form to the soil, e.g. in granular form(soil application). In crops of water rice such granulates can beapplied to the flooded rice field. The compounds of formula I may alsobe applied to seeds (coating) by impregnating the seeds or tubers eitherwith a liquid formulation of the fungicide or coating them with a solidformulation.

A formulation, i.e. a composition comprising the compound of formula Iand, if desired, a solid or liquid adjuvant, is prepared in a knownmanner, typically by intimately mixing and/or grinding the compound withextenders, for example solvents, solid carriers and, optionally,surface-active compounds (surfactants).

The agrochemical formulations will usually contain from 0.1 to 99% byweight, preferably from 0.1 to 95% by weight, of the compound of formulaI, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid orliquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25%by weight, of a surfactant.

Whereas it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

Advantageous rates of application are normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kga.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seeddrenching agent, convenient rates of application are from 10 mg to 1 gof active substance per kg of seeds. The rate of application for thedesired action can be determined by experiments. It depends for exampleon the type of action, the developmental stage of the useful plant, andon the application (location, timing, application method) and can, owingto these parameters, vary within wide limits.

Said methods are particularly effective against the phytopathogenicorganisms of the kingdom Fungi, phylum Basidiomycot, classUredinomycetes, subclass Urediniomycetidae and the order Uredinales(commonly referred to as rusts). Species of rusts having a particularlylarge impact on agriculture include those of the family Phakopsoraceae,particularly those of the genus Phakopsora, for example Phakopsorapachyrhizi, which is also referred to as Asian soybean rust, and thoseof the family Pucciniaceae, particularly those of the genus Pucciniasuch as Puccinia graminis, also known as stem rust or black rust, whichis a problem disease in cereal crops and Puccinia recondita, also knownas brown rust.

An embodiment of said method is a method of protecting crops of usefulplants against attack by a phytopathogenic organism and/or the treatmentof crops of useful plants infested by a phytopathogenic organism, saidmethod comprising simultaneously applying glyphosate, including salts oresters thereof, and at least one compound of formula I, which hasactivity against the phytopathogenic organism to at least one memberselected from the group consisting of the plant, a part of the plant andthe locus of the plant.

Surprisingly, it has now been found that the compounds of formula I, ora pharmaceutical salt thereof, described above have also an advantageousspectrum of activity for the treatment and/or prevention of microbialinfection in an animal.

“Animal” can be any animal, for example, insect, mammal, reptile, fish,amphibian, preferably mammal, most preferably human. “Treatment” meansthe use on an animal which has microbial infection in order to reduce orslow or stop the increase or spread of the infection, or to reduce theinfection or to cure the infection. “Prevention” means the use on ananimal which has no apparent signs of microbial infection in order toprevent any future infection, or to reduce or slow the increase orspread of any future infection.

According to the present invention there is provided the use of acompound of formula I in the manufacture of a medicament for use in thetreatment and/or prevention of microbial infection in an animal. Thereis also provided the use of a compound of formula I as a pharmaceuticalagent. There is also provided the use of a compound of formula I as anantimicrobial agent in the treatment of an animal. According to thepresent invention there is also provided a pharmaceutical compositioncomprising as an active ingredient a compound of formula I, or apharmaceutically acceptable salt thereof, and a pharmaceuticallyacceptable diluent or carrier. This composition can be used for thetreatment and/or prevention of antimicrobial infection in an animal.This pharmaceutical composition can be in a form suitable for oraladministration, such as tablet, lozenges, hard capsules, aqueoussuspensions, oily suspensions, emulsions dispersible powders,dispersible granules, syrups and elixirs. Alternatively thispharmaceutical composition can be in a form suitable for topicalapplication, such as a spray, a cream or lotion. Alternatively thispharmaceutical composition can be in a form suitable for parenteraladministration, for example injection. Alternatively this pharmaceuticalcomposition can be in inhalable form, such as an aerosol spray.

The compounds of formula I are effective against various microbialspecies able to cause a microbial infection in an animal. Examples ofsuch microbial species are those causing Aspergillosis such asAspergillus fumigatus, A. flavus, A. terrus, A. nidulans and A. niger;those causing Blastomycosis such as Blastomyces dermatitidis; thosecausing Candidiasis such as Candida albicans, C. glabrata, C.tropicalis, C. parapsilosis, C. krusei and C. lusitaniae; those causingCoccidioidomycosis such as Coccidioides immitis; those causingCryptococcosis such as Cryptococcus neoformans; those causingHistoplasmosis such as Histoplasma capsulatum and those causingZygomycosis such as Absidia corymbifera, Rhizomucor pusillus andRhizopus arrhizus. Further examples are Fusarium Spp such as Fusariumoxysporum and Fusarium solani and Scedosporium Spp such as Scedosporiumapiospermum and Scedosporium prolificans. Still further examples areMicrosporum Spp, Trichophyton Spp, Epidermophyton Spp, Mucor Spp,Sporothorix Spp, Phialophora Spp, Cladosporium Spp, Petriellidium spp,Paracoccidioides Spp and Histoplasma Spp.

The following non-limiting Examples illustrate the above-describedinvention in greater detail without limiting it.

PREPARATION EXAMPLES Example P1 Preparation ofN′-[6-(4-Chloro-3-trifluoromethyl-phenoxy)-5-(4-fluoro-phenyl)-2-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidinea) Preparation of 3,5-dibromo-6-methyl-pyridin-2-ol

In a 1.5 I five-necked reaction flask equipped with a mechanicalstirrer, protected from sunlight with aluminium foil, 30.0 g of6-methyl-pyridin-2-ol is suspended in 300 ml of dry acetonitrile andstirred at ambient temperature. Under cooling with an ice/water coolingbath, 97.9 g of N-bromo-succinimide (NBS) is added slowly portion-wiseover a time interval of 25 minutes. A minor exothemicity is observed(temperature up to 29° C.). As the suspension is difficult to stir, anadditional 300 ml of dry acetonitrile is added and stirring continued atambient temperature for 1.75 hours. Thereafter, the suspension wasfiltered, the filter cake thoroughly washed with methanol in order toremove the succinimide, and dried to give 64.1 g of the compound as awhite solid (m.p. >225° C.).

b) Preparation of 3-bromo-6-methyl-pyridin-2-ol

In a 1.5 I five-necked reaction flask (flame-dried), 63.1 g of3,5-dibromo-6-methyl-pyridin-2-ol is suspended in 300 ml of dry THF andstirred under argon at ambient temperature. The reaction mixture iscooled down to −78 to −80° C. (Et₂O/dry ice cooling bath). 295 ml of a1.6 M solution of n-butyllithium in hexane is added over 2.5 hour,whereby a temperature increase to −74° C. is observed (yellow-orangesuspension). Stirring is continued at −78 to -80° C. for 1 hour. Then,42.6 ml of water is added slowly over 15 minutes. After stirring at −78°C. for 20 minutes, the temperature was allowed to reach ambienttemperature overnight. The next day, the mixture is concentrated invacuo to give a yellow wet solid. After adding 200 ml of an ageous NaClsolution, extraction is done using AcOEt at a pH value of 9 giving 37.2g (gum) after drying the organic phase over sodium sulfate, filtrationand concentration in vacuo and concentrating the water phase in vacuoleads to 70.1 g of a solid. The combined batches thus obtained arepurified by flash chromatography [silica gel (column: h=25 cm, Ø=12 cm)with tert-butylmethylether together with 1 volume % of AcOH]. Thefractions containing predominantly the compound are combined (29.7 galtogether) and suspended in Et₂O at ambient temperature, the mixturestirred, then filtered, the filter cake washed with Et₂O to give 14.7 gof the compound as a white solid after drying (m.p.=212-213° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.35(s, 3H), 5.97(d, 1H), 7.71(d, 1H),12.35(broad, 1H).

c): Preparation of 3-bromo-6-methyl-5-nitro-pyridin-2-ol

In a 500 ml single-necked round-bottomed flask, 230 ml of a 65% ageousHNO₃ solution is added and stirred under cooling (ice/water coolingbath). 7.00 g of 3-bromo-6-methyl-pyridin-2-ol 2 at ambient temperatureis introduced portion-wise. Stirring is continued for 3.5 hours atambient temperature. After pouring the mixture into 200 ml of anice/water mixture (pH 1), the water phase is extracted with AcOEt. Theorganic phase is washed twice with water brought to pH 4 by addingageous NaOH solution (pH meter), then dried over sodium sulfate,filtered and concentrated in vacuo to give 7.52 g of a yellow solid.This crude material is suspended in diethyl ether and stirred for 1 hourat ambient temperature, filtered, washed with the same solvent and driedto give 3.89 g of the compound as a yellow-orange solid (m.p. >220° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.86(s, 3H), 8.66(s, 1H), 12.75(broad, 1H).

d) Preparation of 3-bromo-2-chloro-6-methyl-5-nitro-pyridine

In a 100 ml single-necked round-bottomed flask equipped with acondensor, 4.36 g of the pyridone is introduced into 17 ml ofphosphorous oxide chloride (brown suspension). This mixture is thenstirred under heating to reflux for 7 h. After cooling the mixture toambient temperature, it is concentrated in vacuo at 50° C., followed byadding toluene and concentrating in vacuo for three times, to obtain abrown oily gum. This gum is treated with ice followed by an excess ofsaturated aqueous sodium bicarbonate solution. The extraction is carriedout with AcOEt. The organic phase is dried over sodium sulfate, filteredand concentrated in vacuo to get 3.79 g of a brown solid. Purificationby flash chromatography over a silica gel cartridge (50 g, 150 ml) of asolid deposition with heptane/ethyl acetate 95:5 (v:v) gives 3.32 g ofthe compound as a light yellow solid (m.p.=76-78° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.82(s, 3H), 8.55(s, 1H).

e) Preparation of3-bromo-2-(4-chloro-3-trifluoromethyl-phenoxy)-6-methyl-5-nitro-pyridine

In a 50 mL single-necked round-bottomed flask, 0.13 ml ofhexamethyldisilazane and 1.21 g of 4-chloro-3-trifluoromethyl-phenol aredissolved and stirred in 3.0 ml of dry dioxane under Argon atmosphere atambient temperature. To this mixture, 270 mg of 55% sodium hydridesuspension is added carefully (gas evolution) and stirring is continuedfor 30 minutes. After this, a solution of 1.55 g of3-bromo-2-chloro-6-methyl-5-nitro-pyridine in 4.0 ml of dry dioxane isadded dropwise by syringe and stirring is continued for 22 hours atambient temperature. The reaction is then quenched by the addition of anexcess of a dilute aqueous NaOH solution (pH=12 of water phase) andextraction carried out with cyclohexane. The organic phase is dried oversodium sulfate, filtered and concentrated in vacuo to obtain an orangeoil. Purification by flash chromatography over a silica gel cartridge(50 g, 150 ml) using heptane/ethyl acetate 95:5 (v:v) as eluent gave 480mg of the compound in the form of a wet solid.

¹H NMR (400 MHz, CDCl₃): δ 2.65(s, 3H), 7.07(dd, 1H), 7.55(d, 1H),7.58(d, 1H), 8.65(s, 1H).

f) Preparation of2-(4-chloro-3-trifluoromethyl-phenoxy)-3-(4-fluoro-phenyl)-6-methyl-5-nitro-pyridine

In a 50 mL single-necked round-bottomed flask equipped with a condensor260 mg of3-bromo-2-(4-chloro-3-trifluoromethyl-phenoxy)-6-methyl-5-nitro-pyridineand 97 mg the p-fluorophenyl boronic acid are dissolved and stirred in1.7 ml of dioxane at ambient temperature (yellow solution) under Argonatmosphere. 228 mg K₃PO₄ dissolved in 0.85 ml of H₂O is then added. Themixture is then degassed by stirring under Argon for 15 min. Now, 4.3 mgof tricyclohexylphosphine together with 3.6 mg ofbis(benzylideneacetone)palladium are added. Thereafter, the solution isstirred vigorously at 100° C. for 6.5 h. The dark brown suspension isthen cooled down to ambient temperature, followed by the addition of 10ml of saturated aqueous NH₄Cl solution. This mixture is extracted withAcOEt. The organic phase is dried over Na₂SO₄, filtered and concentratedin vacuo to give 340 mg of a dark brown oil. After purification by flashchromatography [silica gel cartridge (20 g, 60 ml) of a solid depositionwith heptane/ethyl acetate 95:5 (v:v), then 9:1 (v/v)] 120 mg of thecompound is obtained as a yellow oil.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 2:1 (v:v);R_(f) of compound=0.50.

g) Preparation of6-(4-Chloro-3-trifluoromethyl-phenoxy)-5-(4-fluoro-phenyl)-2-methyl-pyridin-3-ylamine

In a 50 mL single-necked round-bottomed flask equipped with a condensor,120 mg of starting material is stirred in 0.50 ml of methanol (lightyellow suspension). Under ice cooling, 0.50 ml of concentrated aqueousHCl is added dropwise by syringe (more precipitation). The ice bath isremoved and 270 mg of anhydrous SnCl₂ is added slowly (light yellowsuspension). Stirring is continued under heating to reflux for 6.5 h(light yellow solution). Then, the resulting mixture is concentrated invacuo to give a beige wet solid. After adding AcOEt, 5 ml of 4 M aqueousNaOH solution is added. After extraction, the organic phase is driedover Na₂SO₄, filtered (sintered glass filter) and the solvent removed invacuo to give 110 mg of the compound in unpurified form (light yellowbrown oil). Purification was done by flash chromatography (silica gelcartridge (20 g, 60 mL) of a solid deposition with heptane/ethyl acetate2:1 (v:v)) to give 60 mg of the compound as a yellow oil. RP HPLC:retention time of compound: 2.10 minutes

h) Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-(4-fluoro-phenyl)-2-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 25 ml single-necked round-bottomed flask, 30 mg ofethylmethylformamide is solubilized in 0.5 ml of dry dichloromethane atambient temperature (colourless solution). Under stirring, 50 mg ofphosphorous oxide chloride is added dropwise by syringe. Stirring atambient temperature is continued for 1.5 hours, whereupon a pink-orangesolution is obtained. After this, 60 mg of the starting materialdissolved in 1 ml of dry dichloromethane is added dropwise by syringe,giving a yellow solution. Stirring is continued at ambient temperaturefor 2 hours. The mixture is then poured onto ice/water (pH=2, waterphase). 2 M aqueous NaOH is then added to get a pH of about 11 andstirring is continued for 5 minutes. The mixture is then extracted withtwo 10 ml portions of diethyl ether. The combined organic phases arethen dried over sodium sulfate, filtered and the solvent is removed invacuo to obtain 80 mg of the compound in unpurified form as a yellowoil. RP HPLC: Retention time of compound: 1.55 minutes.

Example P2 Preparation ofN′-[5-bromo-6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidinea) Preparation of5-Bromo-6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-pyridin-3-ylamine

In a 50 ml single-necked round-bottomed flask equipped with a condensor,140 mg of crude3-bromo-2-(4-chloro-3-trifluoromethyl-phenoxy)-6-methyl-5-nitro-pyridineis stirred in 0.50 ml of methanol (yellow suspension). Under coolingwith an ice/water bath, 0.50 ml of concentrated aqueous HCl is addeddropwise by syringe (precipitation). The ice bath is removed and 322 mgof anhydrous SnCl₂ is added in portions. Stirring is continued underheating to reflux for 4.5 h (yellow solution). After cooling the mixtureto ambient temperature, it is concentrated in vacuo to give a yellowoil.

After adding AcOEt, 5 ml of 4 M aqueous NaOH solution is added (pH 12).After extraction, the AcOEt phase is dried over Na₂SO₄, filtered and thesolvent removed in vacuo to give 150 mg of a yellow oil. Purificationwas done by flash chromatography [silica gel cartridge (20 g, 60 ml) ofa solid deposition with heptane/ethyl acetate 2:1 (v:v)] to give 80 mgof the compound in the form of a light yellow solid. RP HPLC: Retentiontime of compound: 2.04 minutes.

b) Preparation ofN′-[5-bromo-6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 25 ml single-necked round-bottomed flask, 36.5 mg ofethylmethylformamide is solubilized in 0.5 ml of dry dichloromethane atambient temperature (colourless solution). Under stirring, 0.038 ml ofphosphorous oxide chloride is added dropwise by syringe. Stirring atambient temperature is continued for 1.75 hours, whereupon a pink-orangesolution is obtained. To this solution, 80 mg of5-bromo-6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-pyridin-3-ylaminedissolved in 1.0 ml of dry dichloromethane is added dropwise by syringe,giving a yellow solution. Stirring is continued at an ambienttemperature for 45 minutes. The mixture is then poured into ice/water(pH=2, water phase). 2 M aqueous NaOH is then added to get a pH of about11 and stirring is continued for 10 minutes. The mixture is thenextracted with two 10 ml portions of diethyl ether. The combined organicphases are then dried over sodium sulfate, filtered and the solvent isremoved in vacuo to obtain 80 mg of the compound as a yellow oil(mixture of E and Z isomer).

¹H NMR (400 MHz, CDCl₃): δ 1.15-1.35(broad, 3H), 2.34(s, 3H), 3.03(s,3H), 3.25-3.60(broad, 2H), 7.16 and 7.19(dd, 1H), 7.35(s, 1H), 7.42(m,1H), 7.45(m, 1H), 7.30-7.55(broad, 1H).

TLC: Plates: Merck DC-Platrd, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 2:1 (v:v);R_(f) of compound=0.27.

Example P3 Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-5-trimethylsilanylethynyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidinea) Preparation of2-(4-chloro-3-trifluoromethyl-phenoxy)-6-methyl-5-nitro-3-trimethylsilanylethynyl-pyridine

In a 50 ml single-necked round-bottomed flask equipped with a condensor220 mg of3-bromo-2-(4-chloro-3-trifluoromethyl-phenoxy)-6-methyl-5-nitro-pyridineis dissolved in 4.0 ml of diisopropylamine and the solution is stirredat ambient temperature under Argon atmosphere. After 20 minutes, 15 mgof cuprous iodide and 56 mg of bis(triphenylphosphin)palladiumdichloride are added. This is followed by the dropwise addition of 0.081ml of ethynyltrimethylsilane. The red solution thus obtained is stirredat 70° C. for 5 h. After cooling the mixture to ambient temperature, itis concentrated in vacuo to obtain 490 mg of a brown solid. Purificationof this crude product was carried out by flash chromatography over asilica gel cartridge (20 g; 60 ml) of a solid deposition, withheptane/ethyl acetate 98:2 (v:v) to obtain 40 mg of the compound as abrown oil.

TLC: Plates: Merck DC-Platten, Kieselgel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 2:1 (v:v);R_(f) of compound=0.63.

b) Preparation of6-(4-chloro-3-trifluoromethyl-phenoxy)-5-ethynyl-2-methyl-pyridin-3-ylamine

In a 50 ml single-necked round-bottomed flask equipped with a condensor,35 mg of2-(4-chloro-3-trifluoromethyl-phenoxy)-6-methyl-5-nitro-3-trimethylsilanylethynyl-pyridineis stirred in 0.50 ml of methanol. Under cooling with an ice/water bath,0.50 ml of concentrated aqueous HCl is added dropwise by syringe (someprecipitation is observed). The ice bath is removed and 77 mg ofanhydrous SnCl₂ is added in portions. Stirring is continued underheating to reflux for 2 h. After cooling the mixture to ambienttemperature, it is concentrated in vacuo to give a brown solid. Afteradding AcOEt, 5 ml of 4 M aqueous NaOH solution is added (pH 12).Following extraction, the AcOEt phase is dried over Na₂SO₄, filtered andthe solvent removed in vacuo to give 30 mg a brown oil. Purification wasdone by flash chromatography [silica gel cartridge (5 g, 20 ml) withheptane/ethyl acetate 3:1 (v:v)] to give 7 mg of a 1. fraction(6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-5-trimethylsilanylethynyl-pyridin-3-ylamine)and 15 mg of a 2. fraction of the compound as a brown solid. RP HPLC:Retention time of compound: 1.87 minutes.

c) Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-5-trimethylsilanylethynyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 10 ml single-necked round-bottomed flask, 3.1 mg ofethylmethylformamide is solubilized in 0.25 ml of dry dichloromethane atambient temperature (colourless solution). Under stirring, 0.0032 ml ofphosphorous oxide chloride is added dropwise by syringe. Stirring atambient temperature is continued for 1.0 hour, whereupon a pink-orangesolution is obtained. To this solution, 7.0 mg of6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-5-trimethylsilanylethynyl-pyridin-3-ylaminedissolved in 0.75 ml of dry dichloromethane is added dropwise bysyringe, giving a yellow solution. Stirring is continued at roomtemperature for 2.5 hours. The mixture is then poured into ice/water(pH=2, water phase). 2 M aqueous NaOH is then added to get a pH of about11 and stirring is continued for 15 minutes. The mixture is thenextracted with two 10 ml portions of diethyl ether. The combined organicphases are then dried over sodium sulfate, filtered and the solvent isremoved in vacuo to obtain 6.0 mg of the compound as a yellow oil. RPHPLC: retention time of compound: 1.61 minutes.

Example P4 Preparation ofN′-[5-bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-N-ethyl-N-methyl-formamidinea) Preparation of3-bromo-6-methyl-2-(4-methyl-pentyloxy)-5-nitro-pyridine

In a 50 ml single-necked round-bottomed flask, 1.00 g of3-bromo-6-methyl-5-nitro-pyridin-2-ol is dissolved in 4.50 ml of drydioxane and stirred at ambient temperature under Ar (yellow-orangesuspension). 0.593 ml of 4-methyl-1-pentanol together with 2.354 g oftriphenylphosphine are added. Then, 0.801 ml of diethyl azodicarboxylate(DEAD) is added dropwise by syringe over 10 min, during this addition amoderate exothermicity is observed. Stirring is continued at ambienttemperature for 4.5 hours. The reaction mixture is then quenched by theaddition of 10 ml of water (pH=5-6), followed by the extraction withpentane (3×20 mL). The combined organic phases are dried over sodiumsulfate, filtered and the solvent removed in vacuo to give 1.87 g of thecompound as a yellow-orange oil.

TLC: Plates: Merck DC-Platten, Kieselgel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 1:1 NM;R_(f) of compound=0.72.

b) Preparation of5-bromo-2-methyl-6-(4-methyl-pentyloxy)-Pyridin-3-ylamine

In a 50 ml single-necked round-bottomed flask equipped with a condensor,1.36 g of crude 3-bromo-6-methyl-2-(4-methyl-pentyloxy)-5-nitro-pyridineis dissolved in 3.15 ml of methanol and the resulting solution stirred.Under cooling using an ice/water bath, 3.15 ml of concentrated aqueousHCl is added dropwise by syringe (precipitation is observed). The icebath is removed and 2.23 g anhydrous SnCl₂ is added in portions.Stirring is continued under heating to reflux for 5.5 h (yellowsuspension). After cooling this mixture to ambient temperature, it isconcentrated in vacuo to give a yellow solid. After addingdichloromethane, 10 ml of a 4 M aqueous NaOH solution is added (pH 12).After extraction, the organic phase is dried over Na₂SO₄, filtered andthe solvent removed in vacuo to give 1.62 g of a yellow oil.Purification is done by flash chromatography [silica gel cartridge (50g, 150 ml) of a solid deposition with heptane/ethyl acetate 4:1 (v:v)]to give 490 mg of the compound in the form of a yellow oil. RP HPLC:Retention time of compound: 2.12 minutes.

c) Preparation ofN′-[5-bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 50 ml single-necked round-bottomed flask, 182 mg ofethylmethylformamide is solubilized in 3.0 ml of dry dichloromethane(colourless solution). Under stirring, 0.191 ml of phosphorous oxidechloride is added dropwise by syringe at ambient temperature. Stirringat ambient temperature is continued for 1.75 hours, whereupon apink-orange solution is formed. 300 mg of5-bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-ylamine dissolved in1.50 ml of dry dichloromethane is then added dropwise by syringe, thesolution turning yellow. Stirring is continued at ambient temperaturefor 5 hours. The solution is then poured into ice/water (pH=2, waterphase). 2 M aqueous NaOH is added to a pH of about 11 and the mixture isstirred for 10 minutes. The mixture is then extracted with two 10 mlportions of diethyl ether. The combined ether phases are dried oversodium sulfate, filtered and the solvent is removed in vacuo to obtain380 mg of the compound as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.91(d, 6H), 1.15-1.40(m, m, 5 H), 1.61(m,1H), 1.78(m, 2H), 2.38(s, 3H), 3.04(broad, 3H), 3.25-3.60(broad, 2H),4.30(t, 2H), 7.28(s, 1H), 7.30-7-50(broad, 1H). TLC: Plates: MerckDC-Plates, silica gel F₂₅₄, saturated atmosphere in developing tank, UVdetection, eluent: heptane/ethyl acetate 1:1 (v:v); R_(f) ofcompound=0.48.

Example P5 Preparation ofN′-[5-(4-Chloro-phenyl)-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 10 ml single-necked round-bottomed flask equipped with a condensor(equipment flame-dried), 160 mg of crudeN′-[5-bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-N-ethyl-N-methyl-formamidineand 77.2 mg p-chlorophenyl boronic acid are dissolved in 1.20 ml ofdioxane. To this solution, 162 mg of K₃PO₄ in 0.60 ml of water is addedat ambient temperature under Argon atmosphere. The resulting biphasicmixture is degassed under Argon atmosphere for 20 minutes, whereupon 3.0mg of tricyclohexylphosphine and 2.6 mg ofbis(benzylideneacetone)palladium are added. The resulting suspension isvigorously stirred at a temperature of 100° C. for 5 hours. Afterletting the reaction mixture reach ambient temperature, 5.0 ml of asaturated aqueous NH₄Cl solution is added. The water phase is extractedwith AcOEt. The organic phase is dried over sodium sulfate, filtered andthe solvent removed in vacuo to get 220 mg of a yellow oil. Purificationby flash chromatography over a silica gel cartridge (20 g; 60 ml) of asolid deposition with heptane/ethyl acetate 9:1, then 4:1, then 3:2(v:v) gave 80 mg of the compound as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.88(d, 6H); 1.20(t, 3H), 1.23(m, 2H),1.58(m, 1H), 1.72(m, 2H), 2.44(s, 3H), 3.02(s, 3H), 3.15-3.60(broad,2H), 4.29(t, 2H), 7.06(s, 1H), 7.34(d, 2H), 7.42(broad, 1H), 7.52(d,2H).

Example P6 Preparation ofN-ethyl-N-methyl-N′-[2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-formamidine

In a 50 ml single-necked round-bottomed flask (flame dried) 150 mg ofN′-[5-bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-N-ethyl-N-methyl-formamidineis dissolved in 1.0 ml of absolute THF and stirred under Argonatmosphere. The solution is cooled down to −82° C. (dry ice/acetonecooling bath). Under stirring, 0.263 ml of a 1.6 M solution ofn-butyllithium in hexane is added dropwise by syringe. Stirring at −82°C. is continued for 45 min. Then, 0.091 ml of trimethylchlorsilane isadded dropwise by syringe and stirring continued at −82° C. for 3 hours.After this period of time, the reaction mixture is allowed to warm up toambient temperature. Afterwards, the reaction is quenched by theaddition of 0.020 ml of AcOH, followed by 5.0 ml of water. The waterphase is extracted with diethyl ether and the resulting organic phase isdried over sodium sulfate, filtered and the solvent removed in vacuo togive 30 mg of a yellow oil. The aqueous phase is then brought to pH 7 bythe addition of 10 ml of a saturated aqueous solution of NaHCO₃. This isfollowed by extraction using diethyl ether, drying of the organic phase,filtration and concentration in vacuo to give 90 mg of a yellow oil. The2 oily fractions are combined and purified by flash chromatography[silica gel cartridge (20 g, 60 ml) with heptane/ethyl acetate 95:5,then 9:1, then 4:1 (v:v)] to give 30 mg of the compound as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.90(d, 6H), 1.20(t, 3H), 1.33(m, 2H),1.60(m, 1H); 1.76(m, 2H), 2.41(s, 3H), 2.99(s, 3H), 3.20-3.50(broad,1H), 3.35(broad, 1H), 4.18(t, 2H), 6.46(d, 1H), 7.01(d, 1H), 7.38(broad,1H). RP HPLC: Retention time of compound: 1.26 minutes.

Example P7 Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidinea) Preparation of 2-chloro-3-methyl-5-nitro-pyridine

A 350 ml three-necked round-bottomed flask equipped with a magnetic bar,a thermometer, a dropping funnel and a reflux condenser is charged with3-methyl-5-nitro-pyridin-2-ol (23.1 g), and 1,2-dichloroethane (150 ml).Phosphorous oxide chloride (17 ml) is added dropwise. Into this mixtureDMF (11.5 ml) is added dropwise at room temperature. The reactionmixture is heated at 70° C. under stirring for 0.5 hour. After coolingthe mixture to ambient temperature, it is concentrated in vacuo at 50°C., to obtain a brown oily gum. Purification of this gum by flashchromatography over silica gel with hexane/ethyl acetate 7:3 (v:v) gives23.34 g of the compound as a light yellow solid (MP: 40-42° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.55(s, 3H, CH₃), 8.35(d, 1H), 9.11(d, 1H).

b) Preparation of2-(4-chloro-3-trifluoromethyl-phenoxy)-3-methyl-5-nitro-pyridine

A 250 ml two-necked round-bottomed flask equipped with a magnetic bar, athermometer and a reflux condenser is charged with DMF (50 ml),4-chloro-3-trifluoromethyl-phenol (4.6 g),2-chloro-3-methyl-5-nitro-pyridine (4.0 g) and potassium carbonate (6.4g). The reaction mixture is heated at 100° C. for 2.5 hours. Aftercooling the mixture to room temperature it is then poured into water(200 ml). The mixture is then extracted with ethylacetate (2×40 ml). Thecombined organic layers are dried over sodium sulfate, filtered and thesolvent is removed in vacuo to obtain 6.10 g of the compound as yellowsolid (MP: 95-97° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.50(s, 3H, CH₃), 7.30(dxd, 1H), 7.49(d, 1H),7.55(d, 1H), 8.35(d, 1H), 8.80(d, 1H).

c) Preparation of6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-ylamine

A 250 ml two-necked round-bottomed flask equipped with a KPG-stirrer, athermometer and a reflux condenser is charged with ethanol (100 ml),water (10 ml), iron (3.11 g) and hydrochloric acid 37% (0.3 ml). Thereaction mixture is heated at 50° C.2-(4-chloro-3-trifluoromethyl-phenoxy)-3-methyl-5-nitro-pyridine (5.81g) is added portionwise. The mixture was heated at reflux for 2 hours.After cooling the mixture to 50° C. it is filtered through celite. Thefiltrate is poured into water (200 ml) and extracted with ethylacetate(2×50 ml). The combined organic layers are washed with brine (100 ml),dried over sodium sulfate, filtered and the solvent is removed in vacuoto obtain 4.20 g of the compound as yellow solid (MP: 92-94° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.25 (s, 3H, CH₃), 3.55 (s_(br), 2H, NH₂),6.98 (d, 1H), 7.14 (dxd, 1H), 7.38 (d, 1H), 7.45 (d, 1H), 7.52 (d, 1H).

d) Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 25 ml single-necked round-bottomed flask, ethylmethylformamide (350mg) is solubilized in dry dichloromethane (4 ml) at ambient temperature(colourless solution). Under stirring phosphorous oxide chloride (0.4ml) is added dropwise by syringe. Stirring at ambient temperature iscontinued for 1 hour, whereupon a pink-orange solution is obtained. Tothis solution,6-(4-Chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-ylamine (0.6g) dissolved in 1.0 ml of dry dichloromethane is added dropwise bysyringe, giving a yellow solution. Stirring is continued at an ambienttemperature for 1 hour. The mixture is then poured into ice/water (pH=2,water phase). 2 M aqueous NaOH is then added to get a pH of about 11 andstirring is continued for 10 minutes. The mixture is then extracted withdichloromethane (2×50 ml). The combined organic phases are then driedover sodium sulfate, filtered and the solvent is removed in vacuo.Purification of this gum by flash chromatography over silica gel withhexane/ethyl acetate 1:2 (v:v) gives 0.52 g of the compound as a yellowoil.

¹H NMR (400 MHz, CDCl₃): δ 1.19-1.24(t, 3, CH₃), 2.28(s, 3H, CH₃),3.00(s, 3H, CH₃), 3.28-3.53(m, 2H, CH₂), 7.15-7.26(m, 2H), 7.40(d, 1H),7.46(d, 1H), 7.55(s_(br), 1H), 7.65(d, 1H).

Example P8 Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-pyridin-2-yl-formamidine

In a 25 ml single-necked round-bottomed flask,N-methyl-N-pyridin-2-yl-formamide (0.5 ml) is solubilized in drydichloromethane (4 ml) at ambient temperature (colourless solution).Under stirring phosphorous oxide chloride (0.4 ml) is added dropwise bysyringe. Stirring at ambient temperature is continued for 1 hour. Tothis solution,6-(4-Chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-ylamine (0.6g) dissolved in 1.0 ml of dry dichloromethane is added dropwise bysyringe, giving a yellow solution. Stirring is continued at an ambienttemperature for 1 hour. The mixture is then poured into ice/water (pH=2,water phase). 2 M aqueous NaOH is then added to get a pH of about 11 andstirring is continued for 10 minutes. The mixture is then extracted withdichloromethane (2×50 ml). The combined organic phases are then driedover sodium sulfate, filtered and the solvent is removed in vacuo.Purification of this gum by flash chromatography over silica gel withhexane/ethyl acetate 1:1 (v:v) gives 0.33 g of the compound as a yellowoil.

¹H NMR (400 MHz, CDCl₃): δ 2.34(t, 3, CH₃), 3.53(s, 3H, CH₃), 6.96(d,1H), 7.00(dxd, 1H), 7.21(dxd, 1H), 7.38(d, 1H), 7.45-7.51(m, 2H),7.68-7.72(m, 1H), 7.79(d, 1H), 8.33(dxd, 1H), 9.11(s, 1H).

Example P9 Preparation of[6-(4-chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-yl]-(1-pyrrolidin-1-methylidene)-amine

In a 25 ml single-necked round-bottomed flask,pyrrolidine-1-carbaldehyde (0.4 ml) is solubilized in drydichloromethane (4 ml) at ambient temperature (colourless solution).Under stirring phosphorous oxide chloride (0.4 ml) is added dropwise bysyringe. Stirring at ambient temperature is continued for 1 hour. Tothis solution,6-(4-Chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-ylamine (0.6g) dissolved in 1.0 ml of dry dichloromethane is added dropwise bysyringe, giving a yellow solution. Stirring is continued at an ambienttemperature for 1 hour. The mixture is then poured into ice/water (pH=2,water phase). 2 M aqueous NaOH is then added to get a pH of about 11 andstirring is continued for 10 minutes. The mixture is then extracted withdichloromethane (2×50 ml). The combined organic phases are then driedover sodium sulfate, filtered and the solvent is removed in vacuo.Purification of this gum (0.7 g) by flash chromatography over silica gelwith ethyl acetate gives 0.59 g of the compound as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 1.95 (m_(br), 4H, 2×CH₂), 2.28 (s, 3H, CH₃),3.50-3.55(m, 4H, 2×CH₂), 7.17(dxd, 1H), 7.23(d, 1H), 7.39(d, 1H),7.55(d, 1H), 7.64(d, 1H), 7.75(s, 1H).

Example P10 Preparation ofN′-[6-(3-tert-butyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidinea) Preparation of 2-(3-tert-butyl-phenoxy)-3-methyl-5-nitro-pyridine

A 50 ml two-necked round-bottomed flask equipped with a magnetic bar, athermometer and a reflux condenser is charged with DMF (50 ml),3-tert-butyl-phenol (1.5 g), 2-chloro-3-methyl-5-nitro-pyridine (1.73 g)and potassium carbonate (2.76 g). The reaction mixture is heated at 60°C. for 2 hours. After cooling the mixture to room temperature it is thenpoured into water (200 ml). The mixture is then extracted withethylacetate (2×40 ml). The combined organic layers are dried oversodium sulfate, filtered and the solvent is removed in vacuo.Purification of this crude material by flash chromatography over silicagel with hexane/ethyl acetate 4:1 (v:v) gives 2.55 g of the compound asa yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 1.30(s, 9H, 3×CH₃), 2.48(s, 3H, CH₃),6.95(dxd, 1H), 7.18(m, 1H), 7.30-7.41(m, 2H), 8.30(d, 1H), 8.85(d, 1H).

b) Preparation of 6-(3-tert-butyl-phenoxy)-5-methyl-pyridin-3-ylamine

A 100 ml two-necked round-bottomed flask equipped with a KPG-stirrer, athermometer and a reflux condenser is charged with ethanol (50 ml),water (5 ml), iron (1.43 g) and hydrochloric acid 37% (0.2 ml). Thereaction mixture is heated at 50° C.2-(3-tert-Butyl-phenoxy)-3-methyl-5-nitro-pyridine (2.26 g) was addedportionwise. The mixture is heated at reflux for 3 hours. After coolingthe mixture to 50° C. it is filtered through celite. The filtrate ispoured into water (200 ml) and extracted with ethylacetate (2×50 ml).The combined organic layers are washed with brine (100 ml), dried oversodium sulfate, filtered and the solvent is removed in vacuo.Purification by flash chromatography over silica gel with hexane/ethylacetate 1:1 (v:v) gives 1.10 g of the compound as a brownish solid (MP:83-84° C.).

¹H NMR (400 MHz, CDCl₃): δ 1.32(s, 9H, 3×CH₃), 2.25(s, 3H, CH₃),3.35(s_(br), 2H, NH₂), 6.75(dxd, 1H), 6.80(d, 1H), 7.07-7.15(m, 2H),7.23(d, 1H), 7.55(d, 1H).

c) Preparation ofN′-[6-(3-tert-butyl-phenoxy)-5-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 25 ml single-necked round-bottomed flask, ethylmethylformamide (350mg) is solubilized in dry dichloromethane (4 ml) at ambient temperature(colourless solution). Under stirring phosphorous oxide chloride (0.4ml) is added dropwise by syringe. Stirring at ambient temperature iscontinued for 0.5 hour, whereupon a pink-orange solution is obtained. Tothis solution, 6-(3-tert-butyl-phenoxy)-5-methyl-pyridin-3-ylamine (0.51g) dissolved in 5.0 ml of dry dichloromethane is added dropwise bysyringe, giving a yellow solution. Stirring is continued at an ambienttemperature for 2 hours. The mixture is then poured into ice/water(pH=2, water phase). 2 M aqueous NaOH is then added to get a pH of about11 and stirring is continued for 10 minutes. The mixture is thenextracted with dichloromethane (2×50 ml). The combined organic phasesare then dried over sodium sulfate, filtered and the solvent is removedin vacuo. Purification of this gum by flash chromatography over silicagel with ethyl acetate gives 0.56 g of the compound as a brown oil.

¹H NMR (400 MHz, CDCl₃): δ 1.19-1.24(t, 3, CH₃), 1.30(s, 9H, 3×CH₃),2.28(s, 3H, CH₃), 3.00(s, 3H, CH₃), 3.25-3.35(m_(br), 2H, CH₂),6.80(dxd, 1H), 7.08-7.12(m, 2H), 7.20-7.27(m, 2H), 7.53(s_(br), 1H),7.67(d, 1H).

Example P11 Preparation ofN′-[6-(3,4-Dichloro-phenoxy)-2,4-diisopropyl-pyridin-3-yl]-N,N-dimethyl-formamidine

A 25 ml single-necked round-bottomed flask, fitted with a refluxcondenser is charged with dimethylformamidedimethylacetale (1.6 g), DMF(10 ml) and 6-(3,4-dichloro-phenoxy)-2,4-diisopropyl-pyridin-3-ylamine(1.70 g). The reaction mixture is heated under reflux and methanol isdistilled off for 2.5 hours. The mixture is then concentrated in vacuoat 50° C. The crude material is crystallised from hexane/toluene acetate4:1 (v:v): to obtain 1.41 g of the compound as a white solid (MP:102-103° C.).

¹H NMR (400 MHz, CDCl₃): δ 1.11-1.17(2q, 12H, 4×CH₃), 3.20(s, 6H,2×CH₃), 3.08-3.20(m, 2H), 6.08(s, 1H), 6.85(dxd, 1H), 7.14(s, 1H),7.28(d, 1H), 7.37(d, 1H).

Example P12 Preparation ofN′-[6-(2,4-Dichloro-phenoxy)-Pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 25 ml single-necked round-bottomed flask, ethylmethylformamide (350mg) is solubilized in dry dichloromethane (4 ml) at ambient temperature(colourless solution). Under stirring phosphorous oxide chloride (0.4ml) is added dropwise by syringe. Stirring at ambient temperature iscontinued for 1 hour. To this solution,6-(2,4-Dichloro-phenoxy)-pyridin-3-ylamine (0.5 g) dissolved in 1.0 mlof dry dichloromethane is added dropwise by syringe, giving a yellowsolution. Stirring is continued at an ambient temperature for 1 hour.The mixture is then poured into ice/water (pH=2, water phase). 2 Maqueous NaOH is then added to get a pH of about 11 and stirring iscontinued for 10 minutes. The mixture is then extracted withdichloromethane (2×50 ml). The combined organic phases are then driedover sodium sulfate, filtered and the solvent is removed in vacuo.Purification by flash chromatography over silica gel with hexane/ethylacetate 3:4 (v:v) gives 0.31 g of the compound as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 1.18-1.23(t, 3H, CH₃), 2.98(s, 3H, CH₃),3.25-3.51(m_(br), 2H, CH₂), 6.84-6.89(d, 1H), 7.09(d, 1H), 7.23(dxd,1H), 7.35(dxd, 1H), 7.45(d, 1H), 7.50(s_(br), 1H), 7.75(d, 1H).

Example P13 Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidinea) Preparation of 2-chloro-4-methyl-5-nitro-pyridine

A 100 ml three-necked round-bottomed flask equipped with a magnetic bar,a thermometer, a dropping funnel and a reflux condenser is charged with4-methyl-5-nitro-pyridin-2-ol (5.0 g), and 1,2-dichloroethane (30 ml).Phosphorous oxide chloride (3.6 ml) is added dropwise. Into this mixtureDMF (2.5 ml) is added dropwise at ambient temperature. The reactionmixture is heated at 70° C. under stirring for 0.5 hours. After coolingthe mixture to ambient temperature, it is concentrated in vacuo at 50°C., to obtain a brown oily gum. Purification of this gum by flashchromatography over silica gel with hexane/ethyl acetate 7:3 (v:v) gives4.91 g of the compound as a light yellow solid (MP: 35-38° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.68(s, 3H, CH₃), 7.38(d, 1H), 8.98(d, 1H).

b) Preparation of2-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-5-nitro-pyridine

A 250 ml two-necked round-bottomed flask equipped with a magnetic bar, athermometer and a reflux condenser is charged with DMF (30 ml),4-chloro-3-trifluoromethyl-phenol (4.5 g),2-chloro-4-methyl-5-nitro-pyridine (4.0 g) and potassium carbonate (6.4g). The reaction mixture is stirred at ambient temperature for 1 hour,poured into water (300 ml), acidified with HCl 5 molar (15 ml) and thenextracted with ethylacetate (4×50 ml). The combined organic layers arewashed with brine (100 ml), dried over sodium sulfate, filtered and thesolvent is removed in vacuo. Purification by flash chromatography oversilica gel with hexane/ethyl acetate 7:3 (v:v) gives 7.03 g of thecompound as a red solid (MP: 75-80° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.70(s, 3H, CH₃), 6.93(s, 1H), 7.28(dxd, 1H),7.49(d, 1H), 7.56(d, 1H), 8.35(s, 1H).

c) Preparation of6-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-pyridin-3-ylamine

A 100 ml two-necked round-bottomed flask equipped with a KPG-stirrer, athermometer and a reflux condenser is charged with ethanol (50 ml),water (5 ml), iron (1.29 g) and hydrochloric acid 37% (0.2 ml). Thereaction mixture is heated at 50° C.2-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-5-nitro-pyridine (2.4 g)is added portionwise. The mixture is heated at reflux for 1 hour. Aftercooling the mixture to 50° C. is filtered through celite. The filtrateis poured into water (100 ml) and extracted with ethylacetate (2×50 ml).The combined organic layers are washed with brine (100 ml), dried oversodium sulfate, filtered and the solvent is removed in vacuo.Purification by flash chromatography over silica gel with hexane/ethylacetate 1:1 (v:v) gives 1.90 g of the compound as a brownish solid (MP:105-107° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.23(s, 3H, CH₃), 3.50(s_(br), 2H, NH₂),6.75(s, 1H), 7.18(dxd, 1H), 7.40(d, 1H), 7.43(d, 1H), 7.63(d, 1H).

d) Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

In a 25 ml single-necked round-bottomed flask, ethylmethylformamide (349mg) is solubilized in dry dichloromethane (4 ml) at ambient temperature(colourless solution). Under stirring phosphorous oxide chloride (0.37ml) is added dropwise by syringe. Stirring at ambient temperature iscontinued for 1 hour, whereupon a pink-orange solution is obtained. Tothis solution,6-(4-Chloro-3-trifluoromethyl-phenoxy)-4-methyl-pyridin-3-ylamine (605mg) dissolved in 1.0 ml of dry dichloromethane is added dropwise bysyringe, giving a yellow solution. Stirring is continued at an ambienttemperature for 1 hour. The mixture is then poured into ice/water (pH=2,water phase). 2 M aqueous NaOH is then added to get a pH of about 11 andstirring is continued for 10 minutes. The mixture is then extracted withdichloromethane (2×50 ml). The combined organic phases are then driedover sodium sulfate, filtered and the solvent is removed in vacuo.Purification of this gum by flash chromatography over silica gel withhexane/ethyl acetate 1:1 (v:v) gives 0.67 g of the compound as abrownish oil.

¹H NMR (400 MHz, CDCl₃): δ 1.19-1.24(t, 3, CH₃), 2.30(s, 3H, CH₃),3.00(s, 3H, CH₃), 3.28-3.53(m, 2H, CH₂), 6.78(s, 1H), 7.19(dxd, 1H),7.39-7.45(m, 3H), 7.54(s, 1H).

Example P14 Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-pyridin-3-yl]-N-methyl-N-(1-methyl-prop-2-ynyl)-formamidinea) Preparation of N-Methyl-N-(1-methyl-prop-2-ynyl)-formamide

A 350 ml three-necked round-bottomed flask equipped with a magnetic bar,a thermometer, a dean stark water separator and a reflux condenser ischarged with methyl-(1-methyl-prop-2-ynyl)-amine (8.31 g) and toluene(100 ml). Formic acid (6.9 g) is added dropwise. The reaction mixture isheated at reflux for 2 hours. After cooling the mixture to ambienttemperature, it is concentrated in vacuo at 50° C., to obtain a brownliquid. Purification over silica gel with hexane/ethyl acetate 1:1 (v:v)gives 4.83 g of the compound as a brownish liquid.

¹H NMR (400 MHz, CDCl₃): δ 1.38+1.49(2d, 3H, CH₃), 2.30+2.43(2d, 1H,CH), 2.90+2.98(2s, 3H, CH₃), 4.62+5.38(2m, 1H, CH), 6.78(s, 1H),7.99+8.16(2s, 1H).

b) Preparation ofN′-[6-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-pyridin-3-yl]-N-methyl-N-(1-methyl-prop-2-ynyl)-formamidine

In a 25 ml single-necked round-bottomed flask,N-Methyl-N-(1-methyl-prop-2-ynyl)-formamide (223 mg) is solubilized indry dichloromethane (4 ml) at ambient temperature (colourless solution).Under stirring a mixture of phosphorous oxide chloride (0.18 ml) indichloromethane (1 ml) is added dropwise by syringe. Stirring at ambienttemperature is continued for 1 hour. To this solution,6-(4-Chloro-3-trifluoromethyl-phenoxy)-4-methyl-pyridin-3-ylamine (303mg) dissolved in 10 ml of dry dichloromethane is added dropwise bysyringe, giving a yellow solution. Stirring is continued at an ambienttemperature for 3 hours. The mixture is then poured into ice/water(pH=2, water phase). 2 M aqueous NaOH is then added to get a pH of about11 and stirring is continued for 10 minutes. The mixture is thenextracted with dichloromethane (2×50 ml). The combined organic phasesare then dried over sodium sulfate, filtered and the solvent is removedin vacuo. Purification of this gum by flash chromatography over silicagel with hexane/ethyl acetate 3:2 (v:v) gives 198 mg of the compound asa brownish oil.

¹H NMR (400 MHz, CDCl₃): δ 1.38+1.48(2d, 3H, CH₃), 2.20(s, 3H, CH₃),2.30+2.40(2d, 1H, CH), 2.89+2.98(2s, 3H, CH₃), 4.43+5.38(2m, 1H, CH),6.72(s, 1H), 7.15(dxd, 1H), 7.38(d, 1H), 7.42(d, 1H), 7.62(s, 1H),7.98+8.15(2s, 1H).

RP HPLC Method

HPLC from Agilent: HP1100 quaternary HPLC pump, HP1100 VariableWavelength Detector, HP1100 thermostated column compartment and HP1100solvent degasser. A=water with 0.04% HCOOH, B=Acetonitril/Methanol (4:1,v/v)+0.05% HCOOH Column: Phenomenex Gemini C18, 3 micrometer particlesize, 110 Angström, 30×3 mm, Temp: 60° C.

The gradient timetable contains 5 entries which are:

Time A % B % C % D % Flow (ml/min) 0.00 95.0 5.0 0.0 0.0 1.700 2.00 0.0100.0 0.0 0.0 1.700 2.80 0.0 100.0 0.0 0.0 1.700 2.90 95.0 5.0 0.0 0.01.700 3.10 95.0 5.0 0.0 0.0 1.700

Example P15 Preparation of -2-(4-methyl-pentyloxy)-5-nitro-pyridine

In a 350 ml 5-necked reaction flask (mechanical stirrer, droppingfunnel, thermometer), 3-Hydroxy-1H-pyridin-2-one [CA registry number626-06-2] (35.0 g) is suspended in water (120 ml) at an ambienttemperature. Under stirring, sodium hydroxide (13.48 g) is addedportionwise over 10 minutes, whereupon an exothemic reaction isobserved. The mixture is then immersed in a cooling bath (commonsalt/crushed ice) to obtain a temperature of 0° C. Afterwards, dimethylsulfate (41.72 g) is added over 15 minutes while cooling and stirring iscontinued. Thereafter, the cooling bath is removed and the mixture isstirred overnight at room temperature. The mixture is then extractedwith ethyl acetate. The organic phase is dried over sodium sulfate,filtered and the solvent removed in vacuo to give a dark brown viscousmaterial.

This material is taken up in 112 mol of conc. sulfuric acid andtransferred into a 350 ml 5-necked reaction flask. After stirring andcooling in an ice/water bath, a freshly prepared solution of mixed acid[freshly prepared from sulfuric acid (31.7 ml) and fumic nitric acid(31.8 ml)] is added dropwise over 1.5 h while keeping the temperaturebelow 15° C. Stirring is continued at a temperature below 10° C. for anadditional 45 minutes. Then, the mixture is carefully transferred ontoice and then water is added (to give finally 700 ml of water phase). Theresulting precipitate is stirred for 40 minutes, then filtered and thefilter cake washed with water to give 19.6 g of an orange solid afterdrying.

In a 350 ml 5-necked reaction flask equipped with a condensor, asuspension of this intermediate (5.00 g) in dry dioxane (30.0 ml) isstirred at room temperature. First, 1-bromo-4-methylpentane (5.82 g)then silver oxide (13.62 g) is added. The resulting suspension isstirred under heating to refulx for 13.5 h. After cooling to roomtemperature, ethyl acetate (50 ml) is added and the mixture filteredthrough a pad of Hyflo and washed with ethyl acetate (50 ml). Theorganic pahes is washed with water and brine, then, dried over sodiumsulfate, filtered and the solvent removed in vacuo to give 4.00 g of anorange oil. This raw product is purified by chromatography over silicagel (eluent: hexanes/ethyl acetate 9:1 (v:v)). This way 1.49 g of thetitle compound in form of a yellow solid is obtained (MP: 48-49° C.).

¹H NMR (400 MHz, CDCl₃): δ 0.92(d, 6H), 1.32(m, 2 H), 1.62(m, 1H),1.86(m, 2H), 3.96(s, 3H), 4.48(t, 2H), 7.76(d, 1H), 7.68(d, 1H).

LC: UV Detection: 220 nm; R_(t)=2.08 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 1:1 (v:v);R_(f) of title compound=0.63.

Example P16 Preparation of2-Bromo-5-methoxy-6-(4-methyl-pentyloxy)-pyridin-3-ylamine

In a 50 ml three-necked round-bottomed flask equipped with a condensor,5-Methoxy-6-(4-methyl-pentyloxy)-pyridin-3-ylamine (70 mg) is dissolvedin dry acetonitril (0.50 ml) and stirred at room temperature. Understirring, N-bromosuccinimde (55 mg) is added. Stirring is continued for1.25 h under heating to reflux. After this, a 2 M aqueous solution ofsodium hydroxide (20 ml, pH of 10) is added and extraction is done usingether (three times with 20 ml). The organic layer is washed with a 10%aqueous sodium bisulfite solution (20 ml). After drying over sodiumsulfate, the organic layer is filtered and the solvent removed in vacuoto give a 40 mg of a brown gum. After chromatography on silica gel(eluent: hexanes/ethyl acetate 2:1 (v:v), 6.3 mg of the title compoundare obtained in the form of a red oil.

¹H NMR (400 MHz, CDCl₃): δ 0.90(d, 6H), 1.29(m, 2 H), 1.60(m, 1H),1.79(m, 2H), 3.67(s, 3H), 3.81(s, 3H), 4.26(t, 2H), 6.61(s, 1H).

LC: UV Detection: 220 nm; R_(f)=1.94 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 1:2 (v:v);R_(f) of title compound=0.47.

Example P17 Preparation of6-(4-Methyl-pentyloxy)-3-nitro-pyridin-2-ylamine

-   A) In a 100 ml three-necked round-bottomed flask equipped with a    condensor and a thermometer, sodium hydride (2.51 g of a 55%    suspension in mineral oil) is suspended in dry tetrahydrofuran    (15 ml) and hexamethyldisilazane (0.60 ml) is added and the mixture    stirred for 20 minutes at room temperature under argon. Under    stirring, 4-methyl-1-pentanol (7.23 ml) was added dropwise by    syringe over 10 minutes whereupon gas formation and a temperature    increase to 31° C. is observed. Stirring is continued for an    additional 50 minutes.-   B) In a 200 ml five-necked reaction flask equipped with a mechanical    stirrer, dropping funnel, condensor and thermometer,    6-chloro-3-nitro-pyridin-2-ylamine (5.00 g, cf. registry number    27048-04-0) is suspended in dry tetrahydrofuran (15 ml) at room    temperature under argon. Under stirring, the suspension obtained as    described under A), is added in small portions over 15 minutes.    Occasional cooling with an ice/water bath is used to keep the    temperature under 30° C. To make stirring easier more dry    tetrahydrofuran is added (20 ml). Stirring is continued for 3.5 h.    Afterwards, quenching is carried out by carefully adding an excess    of water (50 ml). Extraction is done then by using ether (60 ml    twice). The organic phase is washed with brine, dried over sodium    sulfate, filtered. The solvent is then removed in vacuo to give    10.78 g of a yellow-brown oil. Chromatography on silica gel (eluent:    hexanes/ethyl acetate 97:3 (v:v)) gives then 6.89 g of the title    compound in the form of a yellow solid (MP: 57-58° C.).

¹H NMR (400 MHz, CDCl₃): δ 0.91(d, 6H), 1.28(m, 2 H), 1.60(m, 1H),1.75(m, 2H), 4.28(t, 2H), 4.90-8.20(broad, 2H), 6.11(d, 1H), 8.28(d,1H).

LC: UV Detection: 220 nm; R_(f)=1.97 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.22.

Example P18 Preparation of5-Bromo-6-(4-methyl-pentyloxy)-3-nitro-pyridin-2-ylamine

In a 50 ml three-necked round-bottomed flask equipped with a condensor,6-(4-methyl-pentyloxy)-3-nitro-pyridin-2-ylamine (1.83 g) is dissolvedin dry acetonitril (8.00 ml) and stirred at room temperature underargon. Under stirring, N-bromosuccinimide (1.36 g) is added. Stirring iscontinued for 3.5 h under heating to reflux. After this, water is added(30 ml) and extraction is done using ether (twice with 60 ml each time).The organic layer is washed with a 10% aqueous sodium bisulfite solution(40 ml). After drying over sodium sulfate, the organic layer is filteredand the solvent removed in vacuo to give a 2.41 g of a dark red oil.After chromatography on silica gel (eluent: hexanes/ethyl acetate 94:6(v:v), 1.87 g of the title compound are obtained in the form of a darkred oil.

¹H NMR (400 MHz, CDCl₃): δ 0.92(d, 6H), 1.33(m, 2 H), 1.62(m, 1H),1.81(m, 2H), 4.34(t, 2H), 4.70-8.40(broad, 2H), 8.52(s, 1H).

LC: UV Detection: 220 nm; R_(f)=2.16 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.20.

Preparation of5-Chloro-6-(4-methyl-pentyloxy)-3-nitro-pyridin-2-ylamine:

This compound can be obtained in an analogous from6-(4-methyl-pentyloxy)-3-nitro-pyridin-2-ylamine usingN-chloro-succinimide.

¹H NMR (400 MHz, CDCl₃): δ 0.92(d, 6H), 1.32(m, 2 H), 1.61(m, 1H),1.81(m, 2H), 4.36(t, 2H), 4.80-8.30(broad, 2H), 8.37(s, 1H).

LC: UV Detection: 220 nm; R_(f)=2.13 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.18.

MP: 53-54° C.

Example P19 Preparation of2,5-Dibromo-6-(4-methyl-pentyloxy)-3-nitro-pyridine

-   A) In a 25 ml single-necked round-bottomed flask 1.41 ml of a 48%    ageous hydrobromic acid solution is added dropwise to    dimethylsulfoxide (7.40 ml) under stirring and cooling with an    ice/water bath to keep the temperature at about room temperature.-   B) In a 50 ml three-necked reaction flask with a condensor,    5-bromo-6-(4-methyl-pentyloxy)-3-nitro-pyridin-2-ylamine (1.00 g) is    dissolved in dimethylsulfoxide (3.70 ml). Under stirring, potassium    nitrite (1.07 g) and copper(I) bromide (90 mg) are added. Under    stirring, the temperature is kept between 35 and 38° C. while the    solution obtained under A) is added dropwise over 5 minutes.    Stirring is continued for an additional 18 h within the same    temperature range whereupon a dark brown suspension is obtained.    After cooling to room temperature, the suspension is brought onto a    saturated ageous sodium carbonate solution (70 ml, pH is 8).    Extraction is carried out using ether (three times with 40 ml). The    combined organic phases are dried over sodium sulfate and then    filtered over a pad of silica (on top of a sintered glass filter    disk). After washing with ether the combined ether phases are    concentrated in vacuo to give 790 mg of the title compound in the    form of a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.93(d, 6H), 1.35(m, 2 H), 1.63(m, 1H),1.84(m, 2H), 4.47(t, 2H), 8.43(s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.56.

Example P20 Preparation of3-Bromo-2-(4-methyl-pentyloxy)-5-nitro-6-phenyl-pyridine

In a 50 ml three-necked round-bottomed flask with a condensor,2,5-dibromo-6-(4-methyl-pentyloxy)-3-nitro-pyridine (200 mg) isdissolved in a mixture of toluene (6.00 ml) and ethanol (0.75 ml) underargon. Under stirring, potassium carbonate (159 mg) in water (0.95 ml)is added, whereupon a yellow biphasic mixture is obtained. Phenylboronicacid is added (63.8 mg). Stirring at room temperature is continued for15 minutes while a stream of argon is led over the mixture. After this,tetrakis(triphenylphosphine)-palladium (18.1 mg) is added and thesolution stirred under heating to reflux for 3.5 h. The mixture is thenstirred at room temperature overnight. Then, a saturated ageous solutionof ammonium chloride (25 ml) is added and extraction is carried out withether (twice with 30 ml). The organic phase is dried over sodiumsulfate, filtered and the solvent removed in vacuo to give 220 mg of ayellow oil. After purification on silica gel (eluent: hexanes/ethylacetate gradient from 100:0 to 98:2) 140 mg of an yellow oil isobtained, containing a mixture of the title compound (43%), along withthe two following by-products:

This mixture is ised as such for the following reduction step to obtainthe corresponding anilines.

Example P21 Preparation of5-Bromo-6-(4-methyl-pentyloxy)-2-phenyl-pyridin-3-ylamine

In a 25 ml three-necked reaction flask with a condensor, the mixtureobtained above (140 mg) (containing3-bromo-2-(4-methyl-pentyloxy)-5-nitro-6-phenyl-pyridine (43%),6-(4-methyl-pentyloxy)-3-nitro-2-phenyl-pyridine (35%), and2-(4-methyl-pentyloxy)-5-nitro-3,6-diphenyl-pyridine (21%)) wassolubilized in methanol (0.50 ml). Under stirring and cooling with anice/water bath, 37% ageous hydrochloric acid (0.15 ml) is addeddropwise. After removing the cooling bath, tin powder (88 mg) is added.The resulting suspension is then stirred under heating to reflux for3.25 h. Then, the mixture is allowed to reach room temperature and themethanol is removed in vacuo. To the resulting orange gum, 2 molarageous sodium hydroxide solution is added (10 ml). Extraction is carriedout using ethyl acetate (twice with 20 ml). The organic layer is driedover sodium sulfate, filtered and the solvent is removed in vacuo togive 130 mg of a yellow gum. The raw material is purified bychromatography on silica gel (eluent: hexanes/ethyl acetat 97:3 (v:v)).50 mg of the title compound is obtained in the form of a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.91(d, 6H), 1.33(m, 2 H), 1.61(m, 1H),1.79(m, 2H), 3.56(s, 3H), 4.31(t, 2H), 7.33(s, 1H), 7.37(tt, 1H),7.46(td, 2H), 7.71(dt, 2H).

LC: UV Detection: 220 nm; R_(t)=2.30 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 3:1 (v:v);R_(f) of title compound=0.35.

Along with this, a mixture of the two following compounds in the form ofa yellow oil (53 mg) is isolated as well.

This mixture is used directly for the following step.

Example P22 Preparation ofN-Ethyl-N-methyl-N′-[6-4-methyl-pentyloxyl-2,5-diphenyl-pyridin-3-yl]-formamidine

In a 8 ml Supelco vessel (closed by a septum), ethylmethylformamide(13.7 mg) is solubilized in dry dichloromethane (3.00 ml) at ambienttemperature (colourless solution). Under stirring phosphorous oxidechloride (0.37 ml) is added dropwise by syringe. Stirring at ambienttemperature is continued for 1.5 hour, whereupon a light-orange solutionis obtained. To this solution, 36.2 mg of the mixture of the twoby-products obtained above [consisting of6-(4-methyl-pentyloxy)-2,5-diphenyl-pyridin-3-ylamine and6-(4-methyl-pentyloxy)-2-phenyl-pyridin-3-ylamine] as a solution in drydichloromethane (2.00 ml) is added dropwise by syringe, giving alight-brown solution. Stirring is continued at an ambient temperaturefor 3.5 hours. The mixture is then poured into ice/water. 2 M aqueousNaOH (10 ml) is then added to get a pH of about 12 and stirring iscontinued for 10 minutes. The mixture is then extracted withdichloromethane (2×20 ml). The combined organic phases are then driedover sodium sulfate, filtered and the solvent is removed in vacuo.Purification of the yellow gum by flash chromatography over silica gelwith hexane/ethyl acetate 4:1 (v:v) gives 17.1 mg of the title compoundas a yellow oil (66%).

¹H NMR (400 MHz, CDCl₃): δ 0.90(d, 6H), 1.15(t, 3H), 1.33(m, 2 H),1.59(m, 1H), 1.79(m, 2H), 2.98(s, 3H), 3.10-3.70(broad, 2H), 4.41(t,2H), 7.33(m, 8H), 7.67(dd, 2H), 8.18(dd, 2H).

LC: UV Detection: 220 nm; R_(t)=1.61 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 3:1 (v:v);R_(f) of title compound=0.18.

Example P23 Preparation of2-Bromo-5-chloro-6-(4-methyl-pentyloxy)-3-nitro-pyridine

-   A) In a 25 ml single-necked round-bottomed flask 1.40 ml of a 48%    ageous hydrobromic acid solution is added dropwise to    dimethylsulfoxide (7.30 ml) under stirring and cooling with an    ice/water bath to keep the temperature at about room temperature.-   B) In a 50 ml three-necked reaction flask with a condensor,    5-chloro-6-(4-methyl-pentyloxy)-3-nitro-pyridin-2-ylamine (850 mg)    is dissolved in dimethylsulfoxide (3.70 ml) at room temperature.    Under stirring, potassium nitrite (1.06 g) and copper(I) bromide (89    mg) are added. Under stirring, the temperature is kept between 35    and 38° C. while the solution obtained under A) is added dropwise    over 6 minutes. Stirring is continued for an additional 20 h within    the same temperature range whereupon a dark brown solution is    obtained. After cooling to room temperature, the suspension is    brought onto a saturated ageous sodium carbonate solution (50 ml, pH    is 9). Extraction is carried out using ether (three times with 50    ml). The combined organic phases are dried over sodium sulfate and    then filtered over a pad of silica (on top of a sintered glass    filter disk). After washing with ether the combined ether phases are    concentrated in vacuo to give 810 mg of the title compound in the    form of a yellow oil. After purification by chromatography on silica    gel (eluent: hexanes/ethyl acetate 95:5 (v:v)) 870 mg of the title    compound are obtained in the form of yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.93(d, 6H), 1.35(m, 2 H), 1.63(m, 1H),1.85(m, 2H), 4.48(t, 2H), 8.28(s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.55.

Example P24 Preparation of5-Methoxy-6-(4-methyl-pentyloxy)-pyridin-3-ylamine

In a 25 ml three-necked reaction flask with a condensor,3-Methoxy-2-(4-methyl-pentyloxy)-5-nitro-pyridine is solubilized inmethanol (2.00 ml). Under stirring and cooling with an ice/water bath,37% ageous hydrochloric acid (0.82 ml) is added. After removing thecooling bath, tin powder (470 mg) is added. The resulting suspension isthen stirred under heating to reflux for 3.5 h. Then, the mixture isallowed to reach room temperature and the methanol is removed in vacuo.To the resulting yellow gum, 2 molar ageous sodium hydroxide solution isadded (25 ml). Extraction is carried out using ethyl acetate (twice with30 ml). The organic layer is dried over sodium sulfate, filtered and thesolvent is removed in vacuo to give 350 mg of a brown oil. The rawmaterial is purified by chromatography on silica gel (eluent:hexanes/ethyl acetat 2:1 (v:v)). 170 mg of the title compound (38.5%) isobtained in the form of a red oil.

¹H NMR (400 MHz, CDCl₃): δ 0.90(d, 6H), 1.30(m, 2 H), 1.59(m, 1H),1.81(m, 2H), 3.36(s, 2H), 3.82(s, 3H), 4.27(t, 2H), 6.56(d, 1H), 7.21(d,1H).

LC: UV Detection: 220 nm; R_(t)=1.47 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 1:1 (v:v);R_(f) of title compound=0.15.

Along with this, 70 mg of a mixture of two by-products in the form of abrown oil was obtained as well. This mixture could be separated by asecond chromatography on silica gel (eluent: toluene/acetone 97:3 (v:v))to give the following compounds:

Example P25 Preparation of2-(4-Methyl-pentyloxy)-5-nitro-3,6-bis-trifluoromethyl-pyridine

In a 10 ml single-necked round-bottomed flask equipped with a condensor,2,5-dibromo-6-(4-methyl-pentyloxy)-3-nitro-pyridine (150 mg) isdissolved in dry dichloromethane (1.00 ml). To the reulting yellowsolution, methyl-2,2-difluoro-2-(fluorosulfonyl)-acetate (377 mg),copper(i)-iodide (90 mg) and hexamethylphosphoramide (HMPA) (350 mg) areadded. The resulting suspension is stirred under heating to reflux for 6hours. The progress of the transformation is followed by ¹⁹F-NMR(CDCl₃). Stirring is continued overnight at an ambient temperature.Saturated ammonium chloride solution is then added (30 ml) and themixture extracted with ether (2×20 ml). The combined organic phases arethen dried over sodium sulfate, filtered and the solvent is removed invacuo. Purification of the yellow oil obtained (120 mg) by flashchromatography over silica gel with hexane/ethyl acetate 98:2 (v:v)gives 100 mg of the title compound as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.92(d, 6H), 1.34(m, 2H), 1.63(m, 1H),1.85(m, 2H), 4.59(t, 2H), 8.49(s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane; R_(f) of titlecompound=0.11.

Example P26 Preparation of5-Chloro-6-(4-methyl-pentyloxy)-3-nitro-pyridine-2-carbonitrile

In a 10 ml single-necked round-bottomed flask equipped with an efficientcondensor, 2-bromo-5-chloro-6-(4-methyl-pentyloxy)-3-nitro-pyridine (200mg) is dissolved in dry acetonitrile (3.00 ml). To the reulting yellowsolution, copper(I) cyanide (109 mg) is added. The resulting suspensionis stirred under heating to reflux for 6 hours whereupon a brownsolution is obtained. The progress of the transformation is followed byGC-MS. The mixture is allowed to reaxch ambient temperature. Saturatedammonium chloride solution (20 ml) along with some ice is then added andthe mixture extracted with ether (2×20 ml). The combined organic phasesare then dried over sodium sulfate, filtered and the solvent is removedin vacuo to give 150 mg of the title compound in the form of a yellowoil (89%).

¹H NMR (400 MHz, CDCl₃): δ 0.93(d, 6H), 1.36(m, 2H), 1.63(m, 1H),1.87(m, 2H), 4.54(t, 2H), 8.53(s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 NM;R_(f) of title compound=0.28.

Example P27 Preparation of3-Chloro-2-(4-methyl-pentyloxy)-5-nitro-6-trifluoromethyl-pyridine

In a 10 ml single-necked round-bottomed flask equipped with an efficientcondensor, 2-bromo-5-chloro-6-(4-methyl-pentyloxy)-3-nitro-pyridine (150mg) is dissolved in dry dimethylformamide (1.20 ml). To the reultingyellow solution, methyl-2,2-difluoro-2-(fluorosulfonyl)-acetate (256mg), copper(i)-iodide (102 mg) and hexamethylphosphoramide (HMPA) (400mg) are added. The resulting suspension is stirred and heating to 100°C. for 2 hours. The progress of the transformation is followed by GC-MS.The reaction mixture is allowed to reach room temperature. Saturatedammonium chloride solution is then added (30 ml, pH about 3) and themixture extracted with ether (2×30 ml). The combined organic phases arethen dried over sodium sulfate, filtered through a pad of silica gel andthe solvent is removed in vacuo. Purification of the yellow oil obtained(120 mg) by flash chromatography over silica gel with hexane/ethylacetate 98:2 (v:v) gives 120 mg of the title compound as a yellow oil(83%).

¹H NMR (400 MHz, CDCl₃): δ 0.93(d, 6H), 1.35(m, 2 H), 1.62(m, 1H),1.86(m, 2H), 4.52(t, 2H), 8.26(s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane; R_(f) of titlecompound=0.11.

Example P28 Preparation of 6-Chloro-2-methoxy-3-nitro-pyridine

-   A) In a 50 ml three-necked round-bottomed flask equipped with an    condensor and a thermometer, sodium hydride (2.26 g of a 0.55%    dispersion in mineral oil) is suspended in dry dioxane (10 ml) under    argon. Then, hexamethyldisilazane (0.81 ml)) is added. Under    stirring, dry methanol (2.10 ml) is added dropwise by syringe    (foaming, gas escapes). The temperature is kept below 34° C. by    cooling using an ice/water bath. After the addition, stirring is    continued at an ambient temperature for 50 minutes. To make the    following tranfer of the suspension easier more dioxane is added (10    ml).-   B) In a 200 ml five-necked reaction flask equipped with an    condensor, mechanical stirrer, dropping funnel and thermometer,    2,6-dichloro-3-nitro-pyridine [CA registry number 136901-10-5]    (10.0 g) dissolved in dry dioxane (40 ml) is stirred under argon.    The suspension freshly prepared as described under A), is added    slowly over 12 minutes (again foaming and gas formation). An    ice/water bath is used to keep the temperature below 32° C. Stirring    at an ambient temperature is continued for 2 hours. Progress of    reaction is monitored by thin layer chromatography (cf. below).

Water is then added (50 ml, pH about 8-9) and the mixture extracted withether (2×50 ml). The combined organic phases are then dried over sodiumsulfate, filtered and the solvent is removed in vacuo to give 10.45 g ofa light yellow solid. Purification of the yellow oil obtained (120 mg)by flash chromatography over silica gel with hexane/ethyl acetate 97:3(v:v) gives 8.00 g of the title compound as a light yellow solid (MP:73-74° C., yield: 82%).

¹H NMR (400 MHz, CDCl₃): δ 4.14 (s, 3H), 7.05 (d, 1H), 8.28 (d, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: hexanes/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.33, R_(f) of starting material=0.21.

Only minor amounts of the isomer of the title compound and of thebis-methoxy-pyridine are found.

Example P29 Preparation of2-Methoxy-6-(4-methyl-pentyloxy)-3-nitro-pyridine

-   A) In a 100 ml five-necked reaction flask equipped with an    condensor, mechanical stirrer, dropping funnel and a thermometer,    sodium hydride (1.16 g of a 0.55% dispersion in mineral oil) is    suspended in dry dioxane (20 ml) under argon. Then,    hexamethyldisilazane (0.44 ml) is added and stirring continued for    15 minutes. Under stirring, 4-methyl-1-pentanol (3.33 ml) is added    dropwise by syringe over 5 minutes (foaming, gas escapes, slightly    exothermic). The temperature doesn't go beyond 25° C. Stirring is    continued for 60 minutes at an ambient temperature whereupon a light    yellow suspension is obtained.-   B) Afterwards, 6-chloro-2-methoxy-3-nitro-pyridine dissolved in dry    dioxane (10 ml) is added over 8 minutes (foam and gas formation).    Cooling with an ice/water bath is used to keep the temperature below    28° C. More dry dioxane is added (10 ml) and the suspension stirred    at an ambient temperature overnight. Progress of reaction is    followed by ¹H-NMR of a sample (obtained by a work-up of a small    sample as described below), indicating about 30% of starting    material left. In order to drive the reaction forward, two    additional additions of the alcoholate of 4-methyl-1-pentanol    following the same protocol as given under B): For the first    addition, 0.5 times of the amount given under A) is used and    stirring continued for 1 hour. For the second addition, 0.3 times    the amount described under A) is used and stirring continued for 2.5    hours. Water is then added (50 ml, pH about 10) and the mixture    extracted with ether (2×80 ml). The combined organic phases are then    dried over sodium sulfate, filtered and the solvent is removed in    vacuo to give 6.70 g of an orange-brown oil. Purification by flash    chromatography over silica gel with hexane/ethyl acetate 98:2 (v:v)    gives 2.70 g of a mixture of the title compound (15%) along with    6-methoxy-2-(4-methyl-pentyloxy)-3-nitro-pyridine (85%, shown    below). This mixture is used as such for the following nitro    reduction to obtain the corresponding aniline derivatives.

¹H NMR (400 MHz, CDCl₃) title compound: δ 0.92 (d, 6H), 1.37 (m, 2H),1.62 (m, 1H), 1.85 (m, 2H), 4.10 (s, 3H), 4.37 (t, 2H), 6.35 (d, 1H),8.33 (d, 1H).

¹H NMR (400 MHz, CDCl₃) isomer: δ 0.92 (d, 6H), 1.37 (m, 2H), 1.62 (m,1H), 1.85 (m, 2H), 3.99 (s, 3H), 4.48 (t, 2H), 6.34 (d, 1H), 8.32 (d,1H).

LC: UV Detection: 220 nm; R_(t)=2.12 min (both components).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 NM;R_(f) of title compound and isomer=0.35, R_(f) of startingmaterial=0.33.

Example P30 Preparation of2-Methoxy-6-(4-methyl-pentyloxy)-pyridin-3-ylamine and6-Methoxy-2-(4-methyl-pentyloxy)-Pyridin-3-ylamine

In a 10 ml single-necked round-bottomed flask with a condensor, 400 mgof a mixture consisting of2-methoxy-6-(4-methyl-pentyloxy)-3-nitro-pyridine (15%) and6-methoxy-2-(4-methyl-pentyloxy)-3-nitro-pyridine (85%) is suspended inmethanol (1.50 ml). Under stirring and cooling with an ice/water bath,37% ageous hydrochloric acid (0.66 ml) is added. After removing thecooling bath, tin powder (280 mg) is added. The resulting suspension isthen stirred under heating to reflux for 3.5 h. Then, the mixture isallowed to reach room temperature and the methanol is removed in vacuo.To the resulting dark green gum, 2 molar aqueous sodium hydroxidesolution is added (10 ml, pH about 12). Extraction is carried out usingethyl acetate (2×20 ml). The organic layer is dried over sodium sulfate,filtered and the solvent is removed in vacuo to give 310 mg of a yellowoil. The raw material is purified by chromatography on silica gel(eluent: hexanes/ethyl acetate, gradient from 1:0 to 98:2 (v:v)). 30 mgof the title compound (8.5%) is obtained in the form of a brown oil.

-   Title Compound

¹H NMR (400 MHz, CDCl₃): δ 0.90 (d, 6H), 1.31 (m, 2H), 1.60 (m, 1H),1.75 (m, 2H), 3.37 (broad, 2H), 3.95 (s, 3H), 4.14 (t, 2H), 6.15 (d,1H), 6.93 (d, 1H).

LC: UV Detection: 220 nm; R_(f)=1.69 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.10, R_(f) of starting material=0.35.

Along with the title compound, 250 mg of the isomeric6-methoxy-2-(4-methyl-pentyloxy)-pyridin-3-ylamine in the form of aorange-brown oil is isolated as well (71%).

¹H NMR (400 MHz, CDCl₃): δ 0.91 (d, 6H), 1.33 (m, 2H), 1.61 (m, 1H),1.79 (m, 2H), 3.38 (broad, 2H), 3.82 (s, 3H), 4.32 (t, 2H), 6.14 (d,1H), 6.94 (d, 1H).

LC: UV Detection: 220 nm; R_(f)=1.72 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f)=0.15.

Example P31 Preparation of3-Chloro-6-methoxy-2-(4-methyl-pentyloxy)-5-nitro-pyridine and3-Chloro-2-methoxy-6-(4-methyl-pentyloxy)-5-nitro-pyridine

In a 10 ml three-necked round-bottomed flask equipped with a condensor,2-methoxy-6-(4-methyl-pentyloxy)-3-nitro-pyridine (15%) and6-methoxy-2-(4-methyl-pentyloxy)-3-nitro-pyridine (85%) (250 mg) isdissolved in dry acetonitril (1.00 ml) and stirred at room temperature.Under stirring, N-chlorosuccinimide (131 mg) is added. Stirring iscontinued for 3.5 h under heating to reflux. After cooling to roomtemperature, water is added (5 ml, pH about 6) and extraction is doneusing ether (2×10 ml). The organic layer is washed with a 10% ageoussodium bisulfite solution (10 ml). After drying over sodium sulfate, theorganic layer is filtered and the solvent removed in vacuo to give a 250mg of a yellow solid. After chromatography on silica gel (eluent:hexanes/ethyl acetate 99:1 (v:v)), 230 mg of a dark red oil is obtainedthat has the following composition:

¹H NMR (400 MHz, CDCl₃) of title compound: δ 0.92 (d, 6H), 1.36 (m, 2H),1.62 (m, 1H), 1.85 (m, 2H), 4.10 (s, 3H), 4.46 (t, 2H), 8.42 (s, 1H).

¹H NMR (400 MHz, CDCl₃) of3-chloro-2-methoxy-6-(4-methyl-pentyloxy)-5-nitro-pyridine: δ 0.92 (d,6H), 1.36 (m, 2H), 1.62 (m, 1H), 1.85 (m, 2H), 4.08 (s, 3H), 4.47 (t,2H), 8.41 (s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound and of3-chloro-2-methoxy-6-(4-methyl-pentyloxy)-5-nitro-pyridine=0.43, R_(f)of starting material=0.35.

Example P32 Preparation of5-Chloro-2-methoxy-6-(4-methyl-pentyloxy)-pyridin-3-ylamine,5-Chloro-6-methoxy-2-(4-methyl-pentyloxy)-pyridin-3-ylamine and6-Methoxy-2-(4-methyl-pentyloxy)-pyridin-3-ylamine

In a 50 ml single-necked round-bottomed flask with a condensor, 220 mgof a mixture consisting of3-chloro-6-methoxy-2-(4-methyl-pentyloxy)-5-nitro-pyridine (11%),3-chloro-2-methoxy-6-(4-methyl-pentyloxy)-5-nitro-pyridine (84%) and6-methoxy-2-(4-methyl-pentyloxy)-3-nitro-pyridine (5%) is suspended inmethanol (1.50 ml). Under stirring and cooling with an ice/water bath,37% ageous hydrochloric acid (0.32 ml) is added. After removing thecooling bath, tin powder (181 mg) is added. The resulting suspension isthen stirred under heating to reflux for 2.5 hours. Following the courseof the reaction by thin layer chromatography indicated that no startingmaterials are left. The mixture is then allowed to reach roomtemperature and the methanol is removed in vacuo. To the resultingyellow solid, 2 molar ageous sodium hydroxide solution is added (5 ml,pH about 12). Extraction is carried out using ethyl acetate (2×10 ml).The organic layer is dried over sodium sulfate, filtered and the solventis removed in vacuo to give 170 mg of a yellow oil. The raw material ispurified by chromatography on silica gel (eluent: hexanes/ethyl acetate97:3 (v:v)). This gives 170 mg of5-chloro-6-methoxy-2-(4-methyl-pentyloxy)-pyridin-3-ylamine in pureform, along with 20 mg of a mixture of5-chloro-2-methoxy-6-(4-methyl-pentyloxy)-pyridin-3-ylamine (62%) and6-methoxy-2-(4-methyl-pentyloxy)-pyridin-3-ylamine (38%). The mixturewas used as such for the transformation to obtain the correspondingamidine derivatives.

Title compound(5-chloro-6-methoxy-2-(4-methyl-pentyloxy)-pyridin-3-ylamine)

¹H NMR (400 MHz, CDCl₃): δ 0.91 (d, 6H), 1.33 (m, 2H), 1.61 (m, 1H),1.78 (m, 2H), 3.42 (broad, 2H), 3.91 (s, 3H), 4.31 (t, 2H), 6.99 (s,1H).

LC: UV Detection: 220 nm; R_(f)=2.07 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of isomer=0.28, R_(f) of starting material=0.43.

For the mixture consisting of:

5-chloro-2-methoxy-6-(4-methyl-pentyloxy)-pyridin-3-ylamine (62%)

¹H NMR (400 MHz, CDCl₃): δ 0.91 (d, 6H), 1.32 (m, 2H), 1.61 (m, 1H),1.79 (m, 2H), 3.40 (broad, 2H), 3.93 (s, 3H), 4.27 (t, 2H), 6.98 (s,1H).

LC: UV Detection: 220 nm; R_(f)=2.09 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.18, R_(f) of starting material=0.43.

6-methoxy-2-(4-methyl-pentyloxy)-pyridin-3-ylamine (38%)

¹H NMR (400 MHz, CDCl₃): δ 0.91 (d, 6H), 1.33 (m, 2H), 1.61 (m, 1H),1.79 (m, 2H), 3.40 (broad, 2H), 3.82 (s, 3H), 4.32 (t, 2H), 6.14 (d,1H), 6.94 (d, 1H).

LC: UV Detection: 220 nm; R_(f)=1.72 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 9:1 (v:v);R_(f) of title compound=0.15, R_(f) of starting material=0.35.

Example P33 Preparation of 3-Nitro-2-phenyl-pyridine

In a 250 mL single-necked round-bottomed flask equipped with acondensor, 10.0 g of 2-chloro-3-nitro-pyridine (CA registry number5470-18-8) is dissolved in 75.0 ml of toluene and 9.3 ml of ethanolunder argon. Then, 19.18 g of potassium carbonate in 12.0 ml of water isadded, followed by 7.69 g of phenyl boronic acid. After stirring for 15minutes under a flow of argon, 2.19 g oftetrakis(triphenylphosphine)palladium is added. The mixture is thenstirred for 20 hours under heating to reflux. The dark brown mixture isthen cooled down to ambient temperature, followed by the addition of 100ml of saturated aqueous NH₄Cl solution. This mixture is extracted withAcOEt (2×100 ml). The organic phase is dried over Na₂SO₄, filtered andconcentrated in vacuo to give 15.26 g of a dark brown oil. Afterpurification by flash chromatography [silica gel cartridge (20 g, 60 ml)of a solid deposition with hexane/ethyl acetate 3:2 (v:v), 12.23 g ofthe title compound is obtained as a brown oil.

title compound is obtained as a brown oil.

¹H NMR (400 MHz, CDCl₃): δ 7.46 (m, 4H), 7.56 (m, 2H), 8.13 (dd, 1H),8.85 (dd, 1H).

LC: UV Detection: 220 nm; R_(t)=1.54 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 1:1 (v:v);R_(f) of title compound=0.44, R_(f) of starting material=0.44.

Example P34 Preparation of 3-Nitro-2-phenyl-pyridine-1-oxide

In a 250 mL three-necked round-bottomed flask equipped with athermometer, droppingbfunnel and a condensor, 11.62 g of3-nitro-2-phenyl-pyridine is dissolved in 58.0 ml of dichloromethane.Then, 13.65 g of H₂O₂ urea adduct is added. Under cooling with anice/water bath, 16.40 ml trifluoroacetic acid anhydride is addeddropwise over 25 minutes (temperature below 12° C.). After stirring at10° C. for 45 minutes, the cooling bath is removed and the mixture isstirred at an ambient temperature for 18 hours. Afterwards, 150 ml ofwater is added (pH about 1) and extraction is carried out withdichloromethane (3×100 ml). After washing the organic phase with 10%aqueous sodium sulfite solution, it is dried over Na₂SO₄. Afterpurification by chromatography on a pad of silica gel (eluent: firstdichloromethane, then ethyl acetate), 9.45 g of the title compound isobtained as a yellow-green solid (MP: 116-117° C.).

¹H NMR (400 MHz, CDCl₃): δ 7.42 (m, 3H), 7.50 (m, 3H), 7.64 (dd, 1H),8.50 (dd, 1H).

LC: UV Detection: 220 nm; R_(f)=1.12 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 1:1 (v:v);R_(f) of title compound=0.05, R_(f) of starting material=0.44.

Example P35 Preparation of 6-Chloro-3-nitro-2-phenyl-pyridine

In a 100 ml single-necked round-bottomed flask equipped with acondensor, 5.00 g of 3-nitro-2-phenyl-pyridine-1-oxide is dissolved in25.0 ml dry 1,2-dichloroethane. Phosphorous oxide chloride (3.18 ml) isadded carefully (yellow-orange solution). This mixture is then stirredunder heating to reflux for 17 h. After cooling the mixture to ambienttemperature. Ice/water is added then. The extraction is carried out withdichloromethane (2×50 ml). After washing with brine, the organic phaseis dried over sodium sulfate, filtered and concentrated in vacuo.Purification by flash chromatography over a silica gel cartridge (25 g,150 ml) of a solid deposition with hexane/ethyl acetate 4:1 (v:v) gives2.61 g of the title compound as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 7.46 (m, 4H), 7.56 (m, 2H), 8.10 (d, 1H).

LC: UV Detection: 220 nm; R_(f)=1.78 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 1:1 (v:v);R_(f) of title compound=0.59, R_(f) of starting material=0.05.

Example P36 Preparation of 2-Chloro-6-methyl-5-nitro-nicotinonitril

In a 200 ml five-necked reaction flask equipped with a mechanicalstirrer, dropping funnel, thermometer and a condensor, 10.00 g of6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (CA registry number:4241-27-4) is added slowly to 75.0 ml concentrated sulfuric acid(exothermic). While stirring and cooling with an ice/water bath, mixedacid reagent (freshly prepared from 5.0 ml of concentrated sulfuric and3.40 ml of fuming nitric acid) is added dropwise over 10 minutes. Thismixture is first allowed to reach 25° C. and then stirred at about thistemperature (under occasional cooling initially with an ice/water bath)for 4 hours. The mixture is then carefully poured into ice and add thenwater (250 ml volume altogether). A precipitate begins to form. Afterfiltration, washing with water and drying 750 mg of a yellow solid isisolated being a mixture of6-methyl-5-nitro-2-oxo-1,2-dihydropyridine-3-carbonitrile (39%) and6-methyl-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid amide(61%). This is used directly for the following step.

In a 50 ml single-necked round-bottomed flask equipped with a condensor,the mixture described above is suspended in 3.80 ml of phosphorous oxidechloride. Under stirring this mixture is heated under reflux for 23.5hours (dark brown solution).

After cooling the mixture to ambient temperature, it is concentrated invacuo at 50° C. The resulting gum is treated with ice followed by anexcess of saturated aqueous sodium bicarbonate solution. The extractionis carried out with AcOEt (3×20 ml). The organic phase is dried oversodium sulfate, filtered and concentrated in vacuo to get 600 mg of abrown solid. Purification by flash chromatography over a silica gelcartridge (20 g, 60 ml) of a solid deposition with hexane/ethyl acetate9:1 (v:v) gives 510 mg of the title compound as a light yellow solid(MP: 94-95° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.95 (s, 3H), 8.60 (s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 1:4 (v:v);R_(f) of title compound=0.68, R_(f) of starting material=0.

Example P37 Preparation of2-(4-Chloro-3-trifluoromethyl-phenoxy)-6-methyl-5.nitro-nicotinonitrile

In a 50 ml single-necked round-bottomed flask, 990 mg4-chloro-3-trifluoromethyl-phenol is dissolved in 5.00 ml of drydioxane. Afterwards, 1.73 ml of Hünig's base is added under stirring,followed by 1.00 g of 2-chloro-6-methyl-5-nitro-nicotinonitrile andstirring continued at an ambient temperature for 24 hours (dark violetsuspension). Afterwards, the mixture is filtered through a pad of silicagel on a sintered glass filter disk, followed by washing withdichloromethane. The combined organic phases are concentrated in vacuoto give 2.32 g of a dark violet gum. After purification bychromatography [silica gel cartridge (50 g, 150 ml), eluent:hexanes/ethyl acetate 4:1 (v:v)], 1.53 g of the title compound areobtained in the form of a orange solid (MP: 110-111° C.).

¹H NMR (400 MHz, CDCl₃): δ 2.77 (s, 3H), 7.34 (dd, 1H), 7.60 (m, 2H),8.72 (s, 1H).

LC: UV Detection: 220 nm; R_(t)=2.08 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 2:1 (v:v);R_(f) of title compound=0.54, R_(f) of starting material=0.52.

Example P38 Preparation of6-Methyl-2-(4-methyl-pentyloxy)-5-nitro-nicotinonitrile

In a 12 ml Supelco vessel, to 0.95 ml of 4-methyl-pentan-1-ol is added1.00 g of 2-chloro-6-methyl-5-nitro-nicotinonitrile. After closing thevessel with a septum, the mixture is stirred under heating to reflux(oil bath temperature of 130° C.). The progress of the reaction ismonitored by thin layer chromatography. After 46 hours, an additional0.53 ml of 4-methyl-pentan-1-ol is added and stirring continued underthe specified conditions. After a heating period of 118 hours in total,the mixture is allowed to come to an ambient temperature. Then, thevolatiles are removed in vacuo at a temperature of 50° C. to give 1.08 gof a brown oil. After purification by chromatography [silica gelcartridge (50 g, 100 ml), eluent: hexanes/ethyl acetate 95:5 (v:v)], 690mg of the title compound are obtained in the form of a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.93 (d, 6H), 1.34 (m, 2H), 1.62 (m, 1H),1.85 (m, 2H), 2.87 (s, 3H), 4.52 (t, 2H), 8.59 (s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 2:1 (v:v);R_(f) of title compound=0.59, R_(f) of starting material=0.52.

Example P39 Preparation of 3-Bromo-4-methyl-5-nitro-1H-pyridin-2-one

In a 1000 ml three-necked round-bottomed flask, 5.00 g of4-methyl-5-nitro-1H-pyridin-2-one (CA registry number: 21901-41-7) issuspended in 500 ml of water. Under stirring, the mixture is kept at atemperature of 40° C. while 1.83 ml of elemental bromine is addeddropwise. Stirring at 40° C. is continued for an additional 4 hours.Afterwards, the mixture is cooled to 10° C. and the resultingprecipitate collected by filtration and washed with water (4×). Afterdrying, 6.65 g of the title compound is obtained in the form of a beigesolid (MP: 237-240° C.).

Example P40 Preparation of 3-Bromo-2-chloro-4-methyl-5-nitro-pyridine

In a 25 ml single-necked round-bottomed flask, to 1.72 ml phosphorousoxide chloride kept at a temperature of 5° C., 0.857 ml quinoline and3.40 g of 3-bromo-4-methyl-5-nitro-1H-pyridin-2-one are addedconsecutively. The resulting beige suspension is stirred under heatingto 120° C. whereupon a brown solution is obtained. Stirring is continuedfor 2 hours. Afterwards, the solution is cooled down to an ambienttemperature and poured into water. The resulting precipitate iscollected by filtration, the filter cake washed with water (4×) anddried to give 3.15 g of the title compound in the form of a brown solid(MP: 60-62° C.).

Example P41 Preparation of3-Bromo-2-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-5-nitro-pyridine

In a 250 ml three-necked round-bottomed flask, 4.00 g4-chloro-3-trifluoromethyl-phenol is dissolved in 80 ml of drymethyl-ethyl-ketone. 3.85 g potassium carbonate followed by 4.70 g of3-bromo-2-chloro-4-methyl-5-nitro-pyridine are added. The resultingbrown suspension is heated to 80° C. under stirring for 3 hours.Afterwards, the green suspension is allowed to reach an ambienttemperature and it then poured into water. The mixture is extracted withethyl actetate (3×50 ml). The combined organic phases are washed withbrine, dried over sodium sulfate, filtered and the solvent removed invacuo. After purification of the raw product on silica gel withcyclohexane/ethyl actetae 19:1 (v:v) 7.36 g of the title compound areobtained as a light yellow gum that solidifies upon standing (MP: 73-74°C.).

Example P42 Preparation of244-Chloro-3-trifluoromethyl-phenoxy)-3,4-dimethyl-5-nitro-pyridine

Example P43 Preparation ofN-[5-Bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-formimidic acidmethyl ester

In a 50 ml single-necked round-bottomed flask, 3.00 g5-bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-ylamine is dissolvedin 10 ml of trimethyl-orthoformate. Under stirring the solution isheated to reflux for 8 hours. Afterwards, the reaction mixture isallowed to reach an ambient temperature and the volatile components areremoved in vacuo at 50° C. to give 3.38 g of the title compound in theform of a brown oil.

¹H NMR (400 MHz, CDCl₃): δ 0.91-0.94(d,6H, CH₃), 1.31-1.41(m,2H, CH₂),1.56-1.73(m,1H, CH), 1.76-1.80(m,2H, CH₂), 2.35(s,3H, CH₃), 4.28(s,3H,CH₃), 4.33-4.36(t,2H, CH₂), 7.26(s,1H), 7.75(s,1H).

TLC: Plates: Merck DC-Platten, Kieselgel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: cyclohexane/ethyl acetate 1:1(v:v); R_(f) of title compound=0.73.

Example P44 Preparation ofN-[5-Bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-N′-ethyl-formamidine

In a 50 ml single-necked round-bottomed flask, 540 mg ofN-[5-Bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-formimidic acidmethyl ester is dissolved in 6.60 ml of dry dichloromethane. Understirring at an ambient temperature, 214 mg of ethylamine hydrochloridealong with 0.45 ml of Hünig's base are added. Stirring is continued atroom temperature for 20 hours. Then, the volatiles are removed in vacuoat 50° C. After purification on silica gel (eluent: heptane/ethylacetate 8:1 (v:v) with 5% triethylamine) to give 530 mg of the titlecompound in the form of a brown oil.

¹H NMR (400 MHz, CDCl₃): δ 0.88-0.89 (d,6H, CH₃), 1.22-1.28 (t, 3H, CH₃)1.30-1.36(m,2H, CH₂), 1.57-1.68(m,1H, CH), 1.75-1.82(m,2H, CH₂),3.32-3.40(broad, 2H, CH₂) 2.35(s,3H, CH₃), 4.30-4.34(t,2H, CH₂),4.34-4.71(broad, 1H, NH) 7.28(s,1H), 7.45(s,1H).

TLC: Plates: Merck DC-Platten, Kieselgel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: cyclohexane/ethyl acetate 1:1+5%Triethylamine (v:v); R_(f) of title compound=0.24.

Example P45 Preparation ofN-[5-Bromo-2-methyl-6-(4-methyl-pentyloxy)-Pyridin-3-yl]-N,N-diethyl-formamidine

In a 50 ml single-necked round-bottomed flask, 540 mg ofN-[5-Bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-formimidic acidmethyl ester is dissolved in 6.60 ml of dry dichloromethane. Understirring at an ambient temperature, 0.273 ml of diethylamine is added.Stirring is continued for 44 hours at an ambient temperature.

LC of a sample indicated that about 40% of starting material is stillpresent.

An additional amount of diethylamine is added and stirring is continuedfor an additional 24 hours. Then, the volatiles are removed in vacuo at50° C. After purification on silica gel (eluent: heptane/ethyl acetate8:1 (v:v) with 5% triethylamine) 530 mg of the title compound areobtained in the form of a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.92-0.0.94 (d,6H, CH₃), 1.20-1.25 (t,6H,CH₃) 1.31-1.39(m,2H, CH₂), 1.57-1.67(m,1H, CH), 1.74-1.82(m,2H, CH₂),2.34(s,3H, CH₃) 3.19-3.49(broad, 4H, CH₂), 4.28-4.34(t,2H, CH₂),7.30(s,1H), 7.36(s,1H).

TLC: Plates: Merck DC-Platten, Kieselgel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: cyclohexane/ethyl acetate 1:1(v:v); R_(f) of title compound=0.66.

Example P46 Preparation of3-Bromo-5-isothiocyannato-6-methyl-2-(4-methyl-pentyloxy)-pyridine

In a 50 ml single-necked round-bottomed flask, 800 mg of5-Bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-ylamine in 1.00 ml ofdry dichloromethane (light yellow solution). Under stirring at atemperature below 5° C. (ice/water bath), first triethylamine (46.6 ml)followed by thiophosgene (ClCSCl) (28.5 ml are added dropwise. Stirringis continued at the same temperature for 1.25 hours. Then, water (10 ml)is added and the extraction is carried out with diethyl ether (2×10 ml).After washing with brine, the organic phase is dried over sodiumsulfate, filtered and concentrated in vacuo to give 130 mg of a yellowoil. The material is used as such for the next step.

Example P47 Preparation of3-[5-Bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-1-isopropyl-1-methyl-thiourea

In a 50 ml single-necked round-bottomed flask, 920 mg of3-bromo-5-isothiocyannato-6-methyl-2-(4-methyl-pentyloxy)-pyridine oxideis dissolved in 1.00 ml dry chloroform. Under stirring,isopropyl-ethyl-amine (20.4 mg) is added dropwise at an ambienttemperature. Stirring is continued at the same temperature for 45minutes. Then, 5.00 ml of water is added to the resulting orangesolution. The extraction is carried out with diethyl ether (2×10 ml).After washing with brine, the organic phase is dried over sodiumsulfate, filtered and concentrated in vacuo to give 140 mg of a brownoil. Purification by flash chromatography over a silica gel cartridge(20 g, 60 ml) of a solid deposition with hexane/ethyl acetate 95:5 (v:v)gives 60.0 mg of the title compound as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ 0.92 (d, 6H), 1.24 (d, 6H), 1.34 (m, 2H),1.63 (m, 1H), 1.80 (m, 2H), 2.34 (s, 3H), 3.08 (s, 3H), 4.34 (t, 2H),5.48 (broad, 1H), 6.70 (broad, 1H), 7.70 (s, 1H).

LC: UV Detection: 220 nm; R_(t)=2.19 min.

TLC: Plates: Merck DC-Plates, silica gel F₂₅₄, saturated atmosphere indeveloping tank, UV detection, eluent: heptane/ethyl acetate 4:1 (v:v);R_(f) of title compound=0.22, R_(f) of starting material=0.67.

Example P48 Preparation of5-Amino-2-imidazol-1-yl-6-methyl-nicotinonitrile

In a 5 ml Supelco vessel, 200 mg of2-chloro-6-methyl-5-nitro-nicotinonitrile (140 mg) is solubilized in drydioxane (1.00 ml). After adding 138 mg of imidazole, the mixture wasstirred for 70 hours at an ambient temperature. The, the suspension wasfiltered over a pad of silica gel, the filter cake washed with ethylacetate and the combined organic phases concentrated in vacuo to give240 mg of orange-brown solid.

In a 50 ml single-necked round-bottomed flask, this solid (240 mg) isdissolved in methanol (1.00 ml). Under stirring and cooling with anice/water bath, 1.00 mol of an ageous 27% hydrochloric acid is addeddropwise. After removing the cooling bath, tin powder is added (186 mg).The green-gray suspension is stirred under heating to reflux for 2.45hours. Afterwards, the heating bath is removed and the mixture stirredat an ambient temperature overnight. Then, the volatiles are removed invacuo and 20 ml of a 4 molar ageous sodium hydroxide solution is added.The extraction is done with ethyl acetate (3×15 ml). The organic layeris dried over sodium sulfate, filtered and the solvent is removed invacuo to give 160 mg of an orange-brown solid.

MS: ES+: 200 (M+H)⁺; ES−: 198 (M−H)⁺

LC Methodology Used

Method 1

HP 1100 HPLC from Agilent: solvent degasser, quaternary pump, heatedcolumn compartment and diode-array detector.

Column: Phenomenex Gemini C18, 3

m particle size, 110 Angström, 30×3 mm,

Temp: 60° C.

DAD Wavelength range (nm): 200 to 500

Solvent Gradient: (same for all methods)

A=water+0.05% HCOOH

B=Acetonitril/Methanol (4:1, v/v)+0.04% HCOOH

Time A % B % Flow (ml/min) 0.00 95.0 5.0 1.700 2.00 0.0 100.0 1.700 2.800.0 100.0 1.700 2.90 95.0 5.0 1.700 3.10 95.0 5.0 1.700Method 3

HP 1100 HPLC from Agilent: solvent degasser, binary pump, heated columncompartment and diode-array detector.

Column: Phenomenex Gemini C18, 3

m particle size, 110 Angström, 30×3 mm,

Temp: 60° C.

DAD Wavelength range (nm): 200 to 500

Solvent Gradient: (same as above)

Method 4

HP 1100 HPLC from Agilent: solvent degasser, binary pump, heated columncompartment and wavelength detector.

-   Column: Phenomenex Gemini C18, 3 nm particle size, 110 Angström,    30×3 mm

Temp: 60° C.

Solvent Gradient: (same as above)

MS. Spectra were recorded on a ZMD (Micromass, Manchester UK) or a ZQ(Waters Corp. Milford, Mass., USA) mass spectrometer equipped with anelectrospray source (ESI; source temperature 80 to 100° C.; desolvationtemperature 200 to 250° C.; cone voltage 30 V; cone gas flow 50 L/Hr,desolvation gas flow 400 to 600 L/Hr, mass range: 150 to 1000 Da).

The compounds according to the following tables can be preparedanalogously. The examples which follow are intended to illustrate theinvention and show preferred compounds of formula I and X.

TABLE P Physical data of compounds of formula I and X: Compound No.Structures MS/NMR/melting point in ° C. P.01

¹H NMR (400 MHz, CDCl₃): δ 1.18- 1.23(t, 3H, CH₃), 2.98(s, 3H, CH₃),3.25- 3.51(m_(br), 2H, CH₂), 6.84-6.89(d, 1H), 7.09(d, 1H), 7.23(dxd,1H), 7.35(dxd, 1H), 7.45(d, 1H), 7.50(s_(br), 1H), 7.75(d, 1H). P.02

1H NMR (400 MHz, CDCl₃): δ 1.38 + 1.48(2d, 3H, CH₃), 2.20(s, 3H, CH3),2.30 + 2.40(d, 1H, CH), 2.89 + 2.98(2s, 3H, CH₃), 4.43 + 5.38(2m, 1H,CH), 6.72(s, 1H), 7.15(dxd, 1H), 7.38(d, 1H), 7.42(d, 1H), 7.62(s, 1H),7.98 + 8.15(2s, 1H). P.03

1H NMR (500 MHz, CD3CN): δ 2.92(s, 3H, CH₃), 2.97(s, 3H, CH₃), 6.88(d,1H), 7.13(d, 1H), 7.32(dxd, 1H), 7.36(dxd, 1H), 7.55(d, 1H), 7.60(s,1H), 7.63(d, 1H). P.04

gum P.05

1H NMR (400 MHz, CDCl₃): δ 1.11- 1.17(2q, 12H, 4xCH₃), 3.20(s, 6H,2xCH₃), 3.08-3.20(m, 2H), 6.08(s, 1H), 6.85(dxd, 1H), 7.14(s, 1H),7.28(d, 1H), 7.37(d, 1H). P.06

gum P.07

gum P.08

gum P.09

gum P.10

gum P.11

1H NMR (400 MHz, CDCl3): δ 1.19- 1.24(t, 3, CH₃), 2.30(s, 3H, CH₃),3.00(s, 3H, CH₃), 3.28-3.53(m, 2H, CH₃), 6.78(s, 1H), 7.19(dxd, 1H),7.39- 7.45(m, 3H), 7.54(s, 1H). P.12

gum P.13

1H NMR (400 MHz, CDCl₃): δ 1.95(mbr, 4H, 2xCH₂), 2.28(s, 3H, CH₃),3.50-3.55(m, 4H, 2xCH₂), 7.17(dxd, 1H), 7.23(d, 1H), 7.39(d, 1H),7.55(d, 1H), 7.64(d, 1H), 7.75(s, 1H). P.14

gum P.15

gum P.16

1H NMR (400 MHz, CDCl₃): δ 2.34(t, 3, CH₃), 3.53(s, 3H, CH₃), 6.96(d,1H), 7.00(dxd, 1H), 7.21(dxd, 1H), 7.38(d, 1H), 7.45- 7.51(m, 2H),7.68-7.72(m, 1H), 7.79(d, 1H), 8.33(dxd, 1H), 9.11(s, 1H). P.17

1H NMR (400 MHz, CDCl₃): δ 1.19- 1.24(t, 3, CH₃), 1.30(s, 9H, 3xCH₃),2.28(s, 3H, CH₃), 3.00(s, 3H, CH₃), 3.25- 3.35(mbr, 2H, CH₂), 6.80(dxd,1H), 7.08- 7.12(m, 2H), 7.20-7.27(m, 2H), 7.53(sbr, 1H), 7.67(d, 1H).p.18.

gum P.19

1H NMR (400 MHz, CDCl₃): δ 1.19- 1.24(t, 3, CH₃), 2.28(s, 3H, CH₃),3.00(s, 3H, CH₃), 3.28-3.53(m, 2H, CH₃), 7.15-7.26(m, 2H), 7.40(d, 1H),7.46(d, 1H), 7.55(sbr, 1H), 7.65(d, 1H). P.20

1H NMR (500 MHz, CD₃CN): δ 2.94(s, 3H, CH₃), 2.98(s, 3H, CH₃), 6.90(d,1H), 7.30(m, 1H), 7.36- 7.40(2m, 2H), 7.46(m, 1H), 7.54(m, 1H), 7.62(s,1H), 7.72(d, 1H). P.21

1H NMR (500 MHz, CD₃CN): δ 2.92(s, 3H, CH₃), 2.97(s, 3H, CH₃), 3.75(s,3H, OCH₃), 6.75(d, 1H), 6.91(d, 2H), 6.98(d, 2H), 7.30(dxd, 1H), 7.58(s,1H), 7.65(d, 1H). P.22

1H NMR (500 MHz, CD₃CN): δ 2.90(s, 3H, CH₃), 2.97(s, 3H, CH₃), 6.84(d,1H), 7.02(d, 2H), 7.34(d, 2H), 7.35(dxd, 1H), 7.60(s, 1H), 7.70(d, 1H).P.23

1H NMR (500 MHz, CD₃CN): δ 2.90(s, 3H, CH₃), 2.97(s, 3H, CH₃), 6.87(d,1H), 7.15-7.23(2m, 4H), 7.35(dxd, 1H), 7.58(s, 1H), 7.81(d, 1H). P.24

1H NMR (500 MHz, CD₃CN): δ 2.90(s, 3H, CH3), 2.96(s, 3H, CH3), 6.93(d,1H), 7.21(t, 1H), 7.38(dxd, 1H), 7.45(d, 2H), 7.54(d, 1H), 7.58(s, 1H).P.25

1H NMR (500 MHz, CD₃CN): δ 2.45(s, 3H, SCH₃), 2.92(s, 3H, CH₃), 2.97(s,3H, CH₃), 6.82(d, 1H), 7.02(d, 2H), 7.28(d, 2H), 7.35(dxd, 1H), 7.60(s,1H), 7.70(d, 1H). P.26

1H NMR (400 MHz, CDCl₃): δ 0.91(d, 6H), 1.15-1.40(m, m, 5 H), 1.61(m,1H), 1.78(m, 2H), 2.38(s, 3H), 3.04(broad, 3H), 3.25-3.60(broad, 2H),4.30(t, 2H), 7.28(s, 1H), 7.30-7.50(broad, 1H). P.27

1H NMR (400 MHz, CDCl₃): δ 0.88(d, 6H); 1.20(t, 3H), 1.23(m, 2H),1.58(m, 1H), 1.72(m, 2H), 2.44(s, 3H), 3.02(s, 3H), 3.15-3.60(broad,2H), 4.29(t, 2H), 7.06(s, 1H), 7.34(d, 2H), 7.42(broad, 1H), 7.52(d,2H). P.28

1H NMR (400 MHz, CDCl₃): δ 0.90(d, 6H), 1.20(t, 3H), 1.33(m, 2H),1.60(m, 1H); 1.76(m, 2H), 2.41(s, 3H), 2.99(s, 3H), 3.20-3.50(broad,1H), 3.35(broad, 1H), 4.18(t, 2H), 6.46(d, 1H), 7.01(d, 1H), 7.38(broad,1H). P.29

1H NMR (400 MHz, CDCl₃): δ 1.15- 1.35(broad, 3H), 2.34(s, 3H), 3.03(s,3H), 3.25-3.60(broad, 2H), 7.16 and 7.19(dd, 1H), 7.35(s, 1H), 7.42(m,1H), 7.45(m, 1H), 7.30-7.55(broad, 1H). P.30

RP HPLC: Retention time of compound: 1.55 minutes P.31

RP HPLC: retention time of compound: 1.61 minutes P.32

RP HPLC: retention time of compound: 1.46 and 1.49 minutes P.33

RP HPLC: retention time of compound: 1.44 minutes P.34

RP HPLC: retention time of compound: 1.38 minutes P.35

RP HPLC: retention time of compound: 2.19 minutes P.36

RP HPLC: retention time of compound: 1.11 minutes P.37

78-79° C. intermediate (formula X) P.38

RP HPLC: retention time of compound: 1.35 minutes P.39

93-94° C. P.40

155-156° C. P.41

142-143° C. P.42

92-93° C. P.43

66-67° C. P.44

91-92° C. intermediate (formula X) P.45

RP HPLC: retention time of compound: 1.27 minutes P.46

RP HPLC: retention time of compound: 1.42 minutes P.47

RP HPLC: retention time of compound: 1.45 minutes P.48

RP HPLC: retention time of compound: 1.50 minutes P.49

72-73° C. P.50

82-83° C. P.51

70-71° C. P.52

81-82° C. P.53

RP HPLC: retention time of compound: 1.43 minutes P.54

RP HPLC: retention time of compound: 1.51 minutes P.55

RP HPLC: retention time of compound: 2.31 minutes P.56

RP HPLC: retention time of compound: 2.27 minutes P.57

74-75° C. P.58

RP HPLC: retention time of compound: 1.31 minutes P.59

RP HPLC: retention time of compound: 1.40 minutes P.60

MS (M + 1) 2.96 intermediate (formula X) P.61

RP HPLC: retention time of compound: 1.42 minutes P.62

RP HPLC: retention time of compound: 1.36 minutes P.63

80-82° C. P.64

RP HPLC: retention time of compound: 1.65 minutes P.65

RP HPLC: retention time of compound: 1.41 minutes P.66

RP HPLC: retention time of compound: 1.45 minutes P.67

RP HPLC: retention time of compound: 1.20 minutes P.68

84-85° C. P.69

RP HPLC: retention time of compound: 1.72 minutes P.70

RP HPLC: retention time of compound: 1.32 minutes P.71

RP HPLC: retention time of compound: 1.60 minutes P.72

RP HPLC: retention time of compound: 1.61 minutes P.73

RP HPLC: retention time of compound: 1.33 minutes P.74

RP HPLC: retention time of compound: 2.24 minutes P.75

RP HPLC: retention time of compound: 2.10 minutes P.76

RP HPLC: retention time of compound: 1.35 minutes P.77

RP HPLC: retention time of compound: 1.37 minutes P.78

123-125° C. P.79

RP HPLC: retention time of compound: 1.46 minutes P.80

RP HPLC: retention time of compound: 1.50 minutes P.81

RP HPLC: retention time of compound: 2.22 minutes P.82

RP HPLC: retention time of compound: 1.39 minutes

Table A discloses 526 sets of meanings of the variables R₁, R₂, R₅ andR₆ in a compound of formula I.

TABLE A Meanings for R₁, R₂, R₅ and R₆: Line R₁ R₂ R₆ R₅ A.1.1 CH₃CH₂CH₃ H

A.1.2 CH₃ CH₂CH₃ H

A.1.3 CH₃ CH₂CH₃ H

A.1.4 CH₃ CH₂CH₃ H

A.1.5 CH₃ CH₂CH₃ H

A.1.6 CH₃ CH₂CH₃ H

A.1.7 CH₃ CH₂CH₃ H

A.1.8 CH₃ CH₂CH₃ H

A.1.9 CH₃ CH₂CH₃ H

A.1.10 CH₃ CH₂CH₃ H

A.1.11 CH₃ CH₂CH₃ H

A.1.12 CH₃ CH₂CH₃ H

A.1.13 CH₃ CH₂CH₃ H

A.1.14 CH₃ CH₂CH₃ H

A.1.15 CH₃ CH₂CH₃ H

A.1.16 CH₃ CH₂CH₃ H

A.1.17 CH₃ CH₂CH₃ H

A.1.18 CH₃ CH₂CH₃ H

A.1.19 CH₃ CH₂CH₃ H

A.1.20 CH₃ CH₂CH₃ H

A.1.21 CH₃ CH₂CH₃ H

A.1.22 CH₃ CH₂CH₃ H

A.1.23 CH₃ CH₂CH₃ H

A.1.24 CH₃ CH₂CH₃ H

A.1.25 CH₃ CH₂CH₃ H

A.1.26 CH₃ CH₂CH₃ H

A.1.27 CH₃ CH₂CH₃ H

A.1.28 CH₃ CH₂CH₃ H

A.1.29 CH₃ CH₂CH₃ H

A.1.30 CH₃ CH₂CH₃ H

A.1.31 CH₃ CH₂CH₃ H

A.1.32 CH₃ CH₂CH₃ H

A.1.33 CH₃ CH₂CH₃ H

A.1.34 CH₃ CH₂CH₃ H

A.1.35 CH₃ CH₂CH₃ H

A.1.36 CH₃ CH₂CH₃ H

A.1.37 CH₃ CH₂CH₃ H

A.1.38 CH₃ CH₂CH₃ H

A.1.39 CH₃ CH₂CH₃ H

A.1.40 CH₃ CH₂CH₃ H

A.1.41 CH₃ CH₂CH₃ H

A.1.42 CH₃ CH₂CH₃ H

A.1.43 CH₃ CH₂CH₃ H

A.1.44 CH₃ CH₂CH₃ H

A.1.45 CH₃ CH₂CH₃ H

A.1.46 CH₃ CH₂CH₃ H

A.1.47 CH₃ CH₂CH₃ H

A.1.48 CH₃ CH₂CH₃ H

A.1.49 CH₃ CH₂CH₃ H

A.1.50 CH₃ CH₂CH₃ H

A.1.51 CH₃ CH₂CH₃ H

A.1.52 CH₃ CH₂CH₃ H

A.1.53 CH₃ CH₂CH₃ H

A.1.54 CH₃ CH₂CH₃ H

A.1.55 CH₃ CH₂CH₃ H

A.1.56 CH₃ CH₂CH₃ H

A.1.57 CH₃ CH₂CH₃ H

A.1.58 CH₃ CH₂CH₃ H

A.1.59 CH₃ CH₂CH₃ H

A.1.60 CH₃ CH₂CH₃ H

A.1.61 CH₃ CH₂CH₃ H

A.1.62 CH₃ CH₂CH₃ H

A.1.63 CH₃ CH₂CH₃ H

A.1.64 CH₃ CH₂CH₃ H

A.1.65 CH₃ CH₂CH₃ H

A.1.66 CH₃ CH₂CH₃ H

A.1.67 CH₃ CH₂CH₃ H

A.1.68 CH₃ CH₂CH₃ H

A.1.69 CH₃ CH₂CH₃ H

A.1.70 CH₃ CH₂CH₃ H

A.1.71 CH₃ CH₂CH₃ H

A.1.72 CH₃ CH₂CH₃ H

A.1.73 CH₃ CH₂CH₃ H

A.1.74 CH₃ CH₂CH₃ H

A.1.75 CH₃ CH₂CH₃ H

A.1.76 CH₃ CH₂CH₃ H

A.1.77 CH₃ CH₂CH₃ H

A.1.78 CH₃ CH₂CH₃ H

A.1.79 CH₃ CH₂CH₃ H

A.1.80 CH₃ CH₂CH₃ H

A.1.81 CH₃ CH₂CH₃ H

A.1.82 CH₃ CH₂CH₃ H

A.1.83 CH₃ CH₂CH₃ H

A.1.84 CH₃ CH₂CH₃ H

A.1.85 CH₃ CH₂CH₃ H

A.1.86 CH₃ CH₂CH₃ H

A.1.87 CH₃ CH₂CH₃ H

A.1.88 CH₃ CH₂CH₃ H

A.1.89 CH₃ CH₂CH₃ H

A.1.l90 CH₃ CH₂CH₃ H

A.1.91 CH₃ CH₂CH₃ H

A.1.92 CH₃ CH₂CH₃ H

A.1.93 CH₃ CH₂CH₃ H

A.1.94 CH₃ CH₂CH₃ H

A.1.95 CH₃ CH₂CH₃ H

A.1.96 CH₃ CH₂CH₃ H

A.1.97 CH₃ CH₂CH₃ H

A.1.98 CH₃ CH₂CH₃ H

A.1.99 CH₃ CH₂CH₃ H

A.1.100 CH₃ CH₂CH₃ H

A.1.101 CH₃ CH₂CH₃ H

A.1.102 CH₃ CH₂CH₃ H

A.1.103 CH₃ CH₂CH₃ H

A.1.104 CH₃ CH₂CH₃ H

A.1.105 CH₃ CH₂CH₃ H

A.1.106 CH₃ CH₂CH₃ H

A.1.107 CH₃ CH₂CH₃ H

A.1.108 CH₃ CH₂CH₃ H

A.1.109 CH₃ CH₂CH₃ H

A.1.110 CH₃ CH₂CH₃ H

A.1.111 CH₃ CH₂CH₃ H

A.1.112 CH₃ CH₂CH₃ H

A.1.113 CH₃ CH₂CH₃ H

A.1.114 CH₃ CH₂CH₃ H

A.1.115 CH₃ CH₂CH₃ H

A.1.116 CH₃ CH₂CH₃ H

A.1.117 CH₃ CH₂CH₃ H

A.1.118 CH₃ CH₂CH₃ H

A.1.119 CH₃ CH₂CH₃ H

A.1.120 CH₃ CH₂CH₃ H

A.1.121 CH₃ CH₂CH₃ H

A.1.122 CH₃ CH₂CH₃ H

A.1.123 CH₃ CH₂CH₃ H

A.1.124 CH₃ CH₂CH₃ H

A.1.125 CH₃ CH₂CH₃ H

A.1.126 CH₃ CH₂CH₃ H

A.1.127 CH₃ CH₂CH₃ H

A.1.128 CH₃ CH₂CH₃ H

A.1.129 CH₃ CH₂CH₃ H

A.1.130 CH₃ CH₂CH₃ H

A.1.131 CH₃ CH₂CH₃ H

A.1.132 CH₃ CH₂CH₃ H

A.1.133 CH₃ CH₂CH₃ H

A.1.134 CH₃ CH₂CH₃ H

A.1.135 CH₃ CH₂CH₃ H

A.1.136 CH₃ CH₂CH₃ H

A.1.137 CH₃ CH₂CH₃ H

A.1.138 CH₃ CH₂CH₃ H

A.1.139 CH₃ CH₂CH₃ H

A.1.140 CH₃ CH₂CH₃ H

A.1.141 CH₃ CH₂CH₃ H

A.1.142 CH₃ CH₂CH₃ H

A.1.143 CH₃ CH₂CH₃ H

A.1.144 CH₃ CH₂CH₃ H

A.1.145 CH₃ CH₂CH₃ H

A.1.146 CH₃ CH₂CH₃ H

A.1.147 CH₃ CH₂CH₃ H

A.1.148 CH₃ CH₂CH₃ H

A.1.149 CH₃ CH₂CH₃ H

A.1.150 CH₃ CH₂CH₃ H

A.1.151 CH₃ CH₂CH₃ H

A.1.152 CH₃ CH₂CH₃ H

A.1.153 CH₃ CH₂CH₃ H

A.1.154 CH₃ CH₂CH₃ H

A.1.155 CH₃ CH₂CH₃ H

A.1.156 CH₃ CH₂CH₃ H

A.1.157 CH₃ CH₂CH₃ H

A.1.158 CH₃ CH₂CH₃ H

A.1.159 CH₃ CH₂CH₃ H

A.1.60 CH₃ CH₂CH₃ H

A.1.161 CH₃ CH₂CH₃ H

A.1.162 CH₃ CH₂CH₃ H

A.1.163 CH₃ CH₂CH₃ H

A.1.164 CH₃ CH₂CH₃ H

A.1.165 CH₃ CH₂CH₃ H

A.1.166 CH₃ CH₂CH₃ H

A.1.167 CH₃ CH₂CH₃ H

A.1.168 CH₃ CH₂CH₃ H

A.1.169 CH₃ CH₂CH₃ H

A.1.170 CH₃ CH₂CH₃ H

A.1.171 CH₃ CH₂CH₃ H

A.1.172 CH₃ CH₂CH₃ H

A.1.173 CH₃ CH₂CH₃ H

A.1.174 CH₃ CH₂CH₃ H

A.1.175 CH₃ CH₂CH₃ H

A.1.176 CH₃ CH₂CH₃ H

A.1.177 CH₃ CH₂CH₃ H

A.1.178 CH₃ CH₂CH₃ H

A.1.79 CH₃ CH₂CH₃ H

A.1.180 CH₃ CH₂CH₃ H

A.1.181 CH₃ CH₂CH₃ H

A.1.182 CH₃ CH₂CH₃ H

A.1.183 CH₃ CH₂CH₃ H

A.1.184 CH₃ CH₂CH₃ H

A.1.185 CH₃ CH₂CH₃ H

A.1.186 CH₃ CH₂CH₃ H

A.1.187 CH₃ CH₂CH₃ H

A.1.188 CH₃ CH₂CH₃ H

A.1.189 CH₃ CH₂CH₃ H

A.1.190 CH₃ CH₂CH₃ H

A.1.191 CH₃ CH₂CH₃ H

A.1.192 CH₃ CH₂CH₃ H

A.1.193 CH₃ CH₂CH₃ H

A.1.194 CH₃ CH₂CH₃ H

A.1.195 CH₃ CH₂CH₃ H

A.1.196 CH₃ CH₂CH₃ H

A.1.197 CH₃ CH₂CH₃ H

A.1.198 CH₃ CH₂CH₃ H

A.1.199 CH₃ CH₂CH₃ H

A.1.200 CH₃ CH₂CH₃ H

A.1.201 CH₃ CH₂CH₃ H

A.1.202 CH₃ CH₂CH₃ H

A.1.203 CH₃ CH₂CH₃ H

A.1.204 CH₃ CH₂CH₃ H

A.1.205 CH₃ CH₂CH₃ H

A.1.206 CH₃ CH₂HC₃ H

A.1.207 CH₃ CH₂CH₃ H

A.1.208 CH₃ CH₂CH₃ H

A.1.209 CH₃ CH₂CH₃ H

A.1.210 CH₃ CH₂CH₃ H

A.1.211 CH₃ CH₂CH₃ H

A.1.212 CH₃ CH₂CH₃ H

A.1.213 CH₃ CH₂CH₃ H

A.1.214 CH₃ CH₂CH₃ H

A.1.215 CH₃ CH₂CH₃ H

A.1.216 CH₃ CH₂CH₃ H

A.1.217 CH₃ CH₂CH₃ H

A.1.218 CH₃ CH₂CH₃ H

A.1.219 CH₃ CH₂CH₃ H

A.1.220 CH₃ CH₂CH₃ H

A.1.221 CH₃ CH₂CH₃ H

A.1.222 CH₃ CH₂CH₃ H

A.1.223 CH₃ CH₂CH₃ H

A.1.224 CH₃ CH₂CH₃ H

A.1.225 CH₃ CH₂CH₃ H

A.1.226 CH₃ CH₂CH₃ H

A.1.227 CH₃ CH₂CH₃ H

A.1.228 CH₃ CH₂CH₃ H

A.1.229 CH₃ CH₂CH₃ H

A.1.230 CH₃ CH₂CH₃ H

A.1.231 CH₃ CH₂CH₃ H

A.1.232 CH₃ CH₂CH₃ H H— A.1.233 CH₃ CH₂CH₃ H

A.1.234 CH₃ CH₂CH₃ H

A.1.235 CH₃ CH₂CH₃ H

A.1.236 CH₃ CH₂CH₃ H

A.1.237 CH₃ CH₂CH₃ H

A.1.238 CH₃ CH₂CH₃ H

A.1.239 CH₃ CH₂CH₃ H

A.1.240 CH₃ CH₂CH₃ H

A.1.241 CH₃ CH₂CH₃ H

A.1.242 CH₃ CH₂CH₃ H

A.1.243 CH₃ CH₂CH₃ H

A.1.244 CH₃ CH₂CH₃ H

A.1.245 CH₃ CH₂CH₃ H H₃C— A.1.246 CH₃ CH₂CH₃ H

A.1.247 CH₃ CH₂CH₃ H

A.1.248 CH₃ CH₂CH₃ H

A.1.249 CH₃ CH₂CH₃ H

A.1.250 CH₃ CH₂CH₃ H

A.1.251 CH₃ CH₂CH₃ H

A.1.252 CH₃ CH₂CH₃ H

A.1.253 CH₃ CH₂CH₃ H

A.1.254 CH₃ CH₂CH₃ H

A.1.255 CH₃ CH₂CH₃ H

A.1.256 CH₃ CH₂CH₃ H

A.1.257 CH₃ CH₂CH₃ H

A.1.258 CH₃ CH₂CH₃ H

A.1.259 CH₃ CH₂CH₃ H

A.1.260 CH₃ CH₂CH₃ H

A.1.261 CH₃ CH₂CH₃ H

A.1.262 CH₃ CH₂CH₃ H

A.1.263 CH₃ CH₂CH₃ H

A.1.264 CH₃ CH₂CH₃ H

A.1.265 CH₃ CH₂CH₃ H

A.1.266 CH₃ CH₂CH₃ H

A.1.267 CH₃ CH₂CH₃ H

A.1.268 CH₃ CH₂CH₃ H

A.1.269 CH₃ CH₂CH₃ H

A.1.270 CH₃ CH₂CH₃ H

A.1.271 CH₃ CH₂CH₃ H

A.1.272 CH₃ CH₂CH₃ H

A.1.273 CH₃ CH₂CH₃ H

A.1.274 CH₃ CH₂CH₃ H

A.1.275 CH₃ CH₂CH₃ H

A.1.276 CH₃ CH₂CH₃ H

A.1.277 CH₃ CH₂CH₃ H

A.1.278 CH₃ CH₂CH₃ H

A.1.279 CH₃ CH₂CH₃ H

A.1.280 CH₃ CH₂CH₃ H

A.1.281 CH₃ CH₂CH₃ H

A.1.282 CH₃ CH₂CH₃ H

A.1.283 CH₃ CH₂CH₃ H

A.1.284 CH₃ CH₂CH₃ H

A.1.285 CH₃ CH₂CH₃ H

A.1.286 CH₃ CH₂CH₃ H

A.1.287 CH₃ CH₂CH₃ H

A.1.288 CH₃ CH₂CH₃ H

A.1.289 CH₃ CH₂CH₃ H

A.1.290 CH₃ CH₂CH₃ H

A.1.291 CH₃ CH₂CH₃ H

A.1.292 CH₃ CH₂CH₃ H

A.1.293 CH₃ CH₂CH₃ H

A.1.294 CH₃ CH₂CH₃ H

A.1.295 CH₃ CH₂CH₃ H

A.1.296 CH₃ CH₂CH₃ H

A.1.297 CH₃ CH₂CH₃ H

A.1.298 CH₃ CH₂CH₃ H

A.1.299 CH₃ CH₂CH₃ H

A.1.300 CH₃ CH₂CH₃ H

A.1.301 CH₃ CH₂CH₃ H

A.1.302 CH₃ CH₂CH₃ H

A.1.303 CH₃ CH₂CH₃ H

A.1.304 CH₃ CH₂CH₃ H

A.1.305 CH₃ CH₂CH₃ H

A.1.306 CH₃ CH₂CH₃ H

A.1.307 CH₃ CH₂CH₃ H

A.1.308 CH₃ CH₂CH₃ H

A.1.309 CH₃ CH₂CH₃ H

A.1.310 CH₃ CH₂CH₃ H

A.1.311 CH₃ CH₂CH₃ H

A.1.312 CH₃ CH₂CH₃ H

A.1.313 CH₃ CH₂CH₃ H

A.1.314 CH₃ CH₂CH₃ H

A.1.315 CH₃ CH₂CH₃ H

A.1.316 CH₃ CH₂CH₃ H

A.1.317 CH₃ CH₂CH₃ H

A.1.318 CH₃ CH₂CH₃ H

A.1.319 CH₃ CH₂CH₃ H

A.1.320 CH₃ CH₂CH₃ H

A.1.321 CH₃ CH₂CH₃ H

A.1.322 CH₃ CH₂CH₃ H

A.1.323 CH₃ CH₂CH₃ H

A.1.324 CH₃ CH₂CH₃ H

A.1.325 CH₃ CH₂CH₃ H

A.1.326 CH₃ CH₂CH₃ H

A.1.327 CH₃ CH₂CH₃ H

A.1.328 CH₃ CH₂CH₃ H

A.1.329 CH₃ CH₂CH₃ H

A.1.330 CH₃ CH₂CH₃ H

A.1.331 CH₃ CH₂CH₃ H

A.1.332 CH₃ CH₂CH₃ H

A.1.333 CH₃ CH₂CH₃ H

A.1.334 CH₃ CH₂CH₃ H

A.1.335 CH₃ CH₂CH₃ H

A.1.336 CH₃ CH₂CH₃ H

A.1.337 CH₃ CH₂CH₃ H

A.1.338 CH₃ CH₂CH₃ H

A.1.339 CH₃ CH₂CH₃ H

A.1.340 CH₃ CH₂CH₃ H

A.1.341 CH₃ CH₂CH₃ H

A.1.342 CH₃ CH₂CH₃ H

A.1.343 CH₃ CH₂CH₃ H

A.1.344 CH₃ CH₂CH₃ H

A.1.345 CH₃ CH₂CH₃ H

A.1.346 CH₃ CH₂CH₃ H

A.1.347 CH₃ CH₂CH₃ H

A.1.348 CH₃ CH₂CH₃ H

A.1.349 CH₃ CH₂CH₃ H

A.1.350 CH₃ CH₂CH₃ H

A.1.351 CH₃ CH₂CH₃ H

A.1.352 CH₃ CH₂CH₃ H

A.1.353 CH₃ CH₂CH₃ H

A.1.354 CH₃ CH₂CH₃ H

A.1.355 CH₃ CH₂CH₃ H

A.1.356 CH₃ CH₂CH₃ H

A.1.357 CH₃ CH₂CH₃ H

A.1.358 CH₃ CH₂CH₃ H

A.1.359 CH₃ CH₂CH₃ H

A.1.360 CH₃ CH₂CH₃ H

A.1.361 CH₃ CH₂CH₃ H

A.1.362 CH₃ CH₂CH₃ H

A.1.363 CH₃ CH₂CH₃ H

A.1.364 CH₃ CH₂CH₃ H

A.1.365 CH₃ CH₂CH₃ H

A.1.366 CH₃ CH₂CH₃ H

A.1.367 CH₃ CH₂CH₃ H

A.1.368 CH₃ CH₂CH₃ H

A.1.369 CH₃ CH₂CH₃ H

A.1.370 CH₃ CH₂CH₃ H

A.1.371 CH₃ CH₂CH₃ H

A.1.372 CH₃ CH₂CH₃ H

A.1.373 CH₃ CH₂CH₃ H

A.1.374 CH₃ CH₂CH₃ H

A.1.375 CH₃ CH₂CH₃ H

A.1.376 CH₃ CH₂CH₃ H

A.1.377 CH₃ CH₂CH₃ H

A.1.378 CH₃ CH₂CH₃ H

A.1.379 CH₃ CH₂CH₃ H

A.1.380 CH₃ CH₂CH₃ H

A.1.381 CH₃ CH₂CH₃ H

A.1.382 CH₃ CH₂CH₃ H

A.1.383 CH₃ CH₂CH₃ H

A.1.384 CH₃ CH₂CH₃ H

A.1.385 CH₃ CH₂CH₃ H

A.1.386 CH₃ CH₂CH₃ H

A.1.387 CH₃ CH₂CH₃ H

A.1.388 CH₃ CH₂CH₃ H

A.1.389 CH₃ CH₂CH₃ H

A.1.390 CH₃ CH₂CH₃ H

A.1.391 CH₃ CH₂CH₃ H

A.1.392 CH₃ CH₂CH₃ H

A.1.393 CH₃ CH₂CH₃ H

A.1.394 CH₃ CH₂CH₃ H

A.1.395 CH₃ CH₂CH₃ H

A.1.396 CH₃ CH₂CH₃ H

A.1.397 CH₃ CH₂CH₃ H

A.1.398 CH₃ CH₂CH₃ H

A.1.399 CH₃ CH₂CH₃ H

A.1.400 CH₃ CH₂CH₃ H

A.1.401 CH₃ CH₂CH₃ H

A.1.402 CH₃ CH₂CH₃ H

A.1.403 CH₃ CH₂CH₃ H

A.1.404 CH₃ CH₂CH₃ H

A.1.405 CH₃ CH₂CH₃ H

A.1.406 CH₃ CH₂CH₃ H

A.1.407 CH₃ CH₂CH₃ H

A.1.408 CH₃ CH₂CH₃ H

A.1.409 CH₃ CH₂CH₃ H

A.1.410 CH₃ CH₂CH₃ H

A.1.411 CH₃ CH₂CH₃ H

A.1.412 CH₃ CH₂CH₃ H

A.1.413 CH₃ CH₂CH₃ H

A.1.414 CH₃ CH₂CH₃ H

A.1.415 CH₃ CH₂CH₃ H

A.1.416 CH₃ CH₂CH₃ H

A.1.417 CH₃ CH₂CH₃ H

A.1.418 CH₃ CH₂CH₃ H

A.1.419 CH₃ CH₂CH₃ H

A.1.420 CH₃ CH₂CH₃ H

A.1.421 CH₃ CH₂CH₃ H

A.1.422 CH₃ CH₂CH₃ H

A.1.423 CH₃ CH₂CH₃ H

A.1.424 CH₃ CH₂CH₃ H

A.1.425 CH₃ CH₂CH₃ H

A.1.426 CH₃ CH₂CH₃ H

A.1.427 CH₃ CH₂CH₃ H

A.1.428 CH₃ CH₂CH₃ H

A.1.429 CH₃ CH₂CH₃ H

A.1.430 CH₃ CH₂CH₃ H

A.1.431 CH₃ CH₂CH₃ H

A.1.432 CH₃ CH₂CH₃ H

A.1.433 CH₃ CH₂CH₃ H

A.1.434 CH₃ CH₂CH₃ H

A.1.435 CH₃ CH₂CH₃ H

A.1.436 CH₃ CH₂CH₃ H

TABLE A Meanings for R₁, R₂, R₅ and R₆ (continued): Line

R₅ A.1.437

A.1.438

A.1.439

A.1.440

A.1.441

A.1.442

A.1.443

A.1.444

A.1.445

A.1.446

A.1.447

A.1.448

A.1.449

A.1.450

A.1.451

A.1.452

A.1.453

A.1.454

A.1.455

A.1.456

A.1.457

A.1.458

A.1.459

A.1.460

A.1.461

A.1.462

A.1.463

A.1.464

A.1.465

A.1.466

A.1.467

A.1.468

A.1.469

A.1.470

A.1.471

A.1.472

A.1.473

A.1.474

A.1.475

A.1.476

A.1.477

A.1.478

A.1.479

A.1.480

A.1.481

A.1.482

A.1.483

A.1.484

A.1.485

A.1.486

A.1.487

A.1.488

A.1.489

A.1.490

A.1.491

A.1.492

A.1.493

A.1.494

A.1.495

A.1.496

A.1.497

A.1.498

A.1.499

A.1.500

A.1.501

A.1.502

A.1.503

A.1.504

A.1.505

A.1.506

A.1.507

A.1.508

A.1.509

A.1.510

A.1.511

A.1.512

A.1.513

A.1.514

A.1.515

A.1.516

A.1.517

A.1.518

A.1.519

A.1.520

A.1.521

A.1.522

A.1.523

A.1.524

A.1.525

A.1.526

The following tables T1 to T151 disclose preferred compounds of formulaI.

Table 1: This table discloses the 526 compounds T1.1.1 to T1.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A. For example, the specific compound T1.1.13 is thecompound of the formula T1, in which each of the variables R₁, R₂, R₅and R₆ has the specific meaning given in the line A.1.13 of Table A:

According to the same system, also all of the other 511 specificcompounds disclosed in the Table 1 as well as all of the specificcompounds disclosed in the Tables 2 to T151 are specified analogously.

Table 2: This table discloses the 526 compounds T2.1.1 to T2.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 3: This table discloses the 526 compounds T3.1.1 to T3.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 4: This table discloses the 526 compounds T4.1.1 to T4.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 5: This table discloses the 526 compounds T5.1.1 to T5.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 6: This table discloses the 526 compounds T6.1.1 to T6.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 7: This table discloses the 526 compounds T7.1.1 to T7.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 8: This table discloses the 526 compounds T8.1.1 to T8.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 9: This table discloses the 526 compounds T9.1.1 to T9.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 10: This table discloses the 526 compounds T10.1.1 to T10.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 11: This table discloses the 526 compounds T11.1.1 to T11.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 12: This table discloses the 526 compounds T12.1.1 to T12.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 13: This table discloses the 526 compounds T13.1.1 to T13.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 14: This table discloses the 526 compounds T14.1.1 to T14.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 15: This table discloses the 526 compounds T15.1.1 to T15.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 16: This table discloses the 526 compounds T16.1.1 to T16.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 17: This table discloses the 526 compounds T17.1.1 to T17.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 18: This table discloses the 526 compounds T18.1.1 to T18.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 19: This table discloses the 526 compounds T19.1.1 to T19.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 20: This table discloses the 526 compounds T20.1.1 to T20.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 21: This table discloses the 526 compounds T21.1.1 to T21.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 22: This table discloses the 526 compounds T22.1.1 to T22.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 23: This table discloses the 526 compounds T23.1.1 to T23.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 24: This table discloses the 526 compounds T24.1.1 to T24.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 25: This table discloses the 526 compounds T25.1.1 to T25.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 26: This table discloses the 526 compounds T26.1.1 to T26.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 27: This table discloses the 526 compounds T27.1.1 to T27.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 28: This table discloses the 526 compounds T28.1.1 to T28.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 29: This table discloses the 526 compounds T29.1.1 to T29.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 30: This table discloses the 526 compounds T30.1.1 to T30.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 31: This table discloses the 526 compounds T31.1.1 to T31.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 32: This table discloses the 526 compounds T32.1.1 to T32.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 33: This table discloses the 526 compounds T33.1.1 to T33.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 34: This table discloses the 526 compounds T34.1.1 to T34.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 35: This table discloses the 526 compounds T35.1.1 to T35.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 36: This table discloses the 526 compounds T36.1.1 to T36.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 37: This table discloses the 526 compounds T37.1.1 to T37.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 38: This table discloses the 526 compounds T38.1.1 to T38.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 39: This table discloses the 526 compounds T39.1.1 to T39.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 40: This table discloses the 526 compounds T40.1.1 to T40.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 41: This table discloses the 526 compounds T41.1.1 to T41.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 42: This table discloses the 526 compounds T42.1.1 to T42.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 43: This table discloses the 526 compounds T43.1.1 to T43.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 44: This table discloses the 526 compounds T44.1.1 to T44.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 45: This table discloses the 526 compounds T45.1.1 to T45.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 46: his table discloses the 526 compounds T46.1.1 to T46.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 47: This table discloses the 526 compounds T47.1.1 to T47.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 48: This table discloses the 526 compounds T48.1.1 to T48.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 49: This table discloses the 526 compounds T49.1.1 to T49.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 50: This table discloses the 526 compounds T50.1.1 to T50.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 51: This table discloses the 526 compounds T51.1.1 to T51.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 52: This table discloses the 526 compounds T52.1.1 to T52.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 53: This table discloses the 526 compounds T53.1.1 to T53.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 54: This table discloses the 526 compounds T54.1.1 to T54.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 55: This table discloses the 526 compounds T55.1.1 to T55.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 56: This table discloses the 526 compounds T56.1.1 to T56.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 57: This table discloses the 526 compounds T57.1.1 to T57.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 58: This table discloses the 526 compounds T58.1.1 to T58.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 59: This table discloses the 526 compounds T59.1.1 to T59.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 60: This table discloses the 526 compounds T60.1.1 to T60.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 61: This table discloses the 526 compounds T61.1.1 to T61.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 62: This table discloses the 526 compounds T62.1.1 to T62.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 63: This table discloses the 526 compounds T63.1.1 to T63.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 64: This table discloses the 526 compounds T64.1.1 to T64.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 65: This table discloses the 526 compounds T65.1.1 to T65.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 66: This table discloses the 526 compounds T66.1.1 to T66.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 67: This table discloses the 526 compounds T67.1.1 to T67.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 68: This table discloses the 526 compounds T68.1.1 to T68.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 69: This table discloses the 526 compounds T69.1.1 to T69.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 70: This table discloses the 526 compounds T70.1.1 to T70.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 71: This table discloses the 526 compounds T71.1.1 to T71.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 72: This table discloses the 526 compounds T72.1.1 to T72.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 73: This table discloses the 526 compounds T73.1.1 to T73.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 74: This table discloses the 526 compounds T74.1.1 to T74.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 75: This table discloses the 526 compounds T75.1.1 to T75.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 76: This table discloses the 526 compounds T76.1.1 to T76.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 77: This table discloses the 526 compounds T77.1.1 to T77.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 78: This table discloses the 526 compounds T78.1.1 to T78.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 79: This table discloses the 526 compounds T79.1.1 to T79.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 80: This table discloses the 526 compounds T80.1.1 to T80.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 81: This table discloses the 526 compounds T81.1.1 to T81.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 82: This table discloses the 526 compounds T82.1.1 to T82.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 83: This table discloses the 526 compounds T83.1.1 to T83.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 84: This table discloses the 526 compounds T84.1.1 to T84.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 85: This table discloses the 526 compounds T85.1.1 to T85.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 86: This table discloses the 526 compounds T86.1.1 to T86.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 87: This table discloses the 526 compounds T87.1.1 to T87.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 88: This table discloses the 526 compounds T88.1.1 to T88.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 89: This table discloses the 526 compounds T89.1.1 to T89.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 90: This table discloses the 526 compounds T90.1.1 to T90.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 91: This table discloses the 526 compounds T91.1.1 to T91.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 92: This table discloses the 526 compounds T92.1.1 to T92.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 93: This table discloses the 526 compounds T93.1.1 to T93.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 94: This table discloses the 526 compounds T94.1.1 to T94.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 95: This table discloses the 526 compounds T95.1.1 to T95.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 96: This table discloses the 526 compounds T96.1.1 to T96.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 97: This table discloses the 526 compounds T97.1.1 to T97.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 98: This table discloses the 526 compounds T98.1.1 to T98.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 99: This table discloses the 526 compounds T99.1.1 to T99.1.526 ofthe formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 100: This table discloses the 526 compounds T100.1.1 to T100.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 101: This table discloses the 526 compounds T101.1.1 to T101.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 102: This table discloses the 526 compounds T102.1.1 to T102.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 103: This table discloses the 526 compounds T103.1.1 to T103.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 104: This table discloses the 526 compounds T104.1.1 to T104.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 105: This table discloses the 526 compounds T105.1.1 to T105.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 106: This table discloses the 526 compounds T106.1.1 to T106.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 107: This table discloses the 526 compounds T107.1.1 to T107.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 108: This table discloses the 526 compounds T108.1.1 to T108.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 109: This table discloses the 526 compounds T109.1.1 to T109.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 110: This table discloses the 526 compounds T110.1.1 to T110.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 111: This table discloses the 526 compounds T111.1.1 to T111.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 112: This table discloses the 526 compounds T112.1.1 to T112.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 113: This table discloses the 526 compounds T113.1.1 to T113.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 114: This table discloses the 526 compounds T114.1.1 to T114.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 115: This table discloses the 526 compounds T115.1.1 to T115.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 116: This table discloses the 526 compounds T116.1.1 to T116.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 117: This table discloses the 526 compounds T117.1.1 to T117.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 118: This table discloses the 526 compounds T118.1.1 to T118.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 119: This table discloses the 526 compounds T119.1.1 to T119.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 120: This table discloses the 526 compounds T120.1.1 to T120.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 121: This table discloses the 526 compounds T121.1.1 to T121.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 122: This table discloses the 526 compounds T122.1.1 to T122.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 123: This table discloses the 526 compounds T123.1.1 to T123.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 124: This table discloses the 526 compounds T124.1.1 to T124.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 125: This table discloses the 526 compounds T125.1.1 to T125.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 126: This table discloses the 526 compounds T126.1.1 to T126.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 127: This table discloses the 526 compounds T127.1.1 to T127.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 128: This table discloses the 526 compounds T128.1.1 to T128.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 129: This table discloses the 526 compounds T129.1.1 to T129.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 130: This table discloses the 526 compounds T130.1.1 to T130.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 131: This table discloses the 526 compounds T131.1.1 to T131.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 132: This table discloses the 526 compounds T132.1.1 to T132.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 133: This table discloses the 526 compounds T133.1.1 to T133.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 134: This table discloses the 526 compounds T134.1.1 to T134.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 135: This table discloses the 526 compounds T135.1.1 to T135.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 136: This table discloses the 526 compounds T136.1.1 to T136.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 137: This table discloses the 526 compounds T137.1.1 to T137.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 138: This table discloses the 526 compounds T138.1.1 to T138.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 139: This table discloses the 526 compounds T139.1.1 to T139.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 140: This table discloses the 526 compounds T140.1.1 to T140.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 141: This table discloses the 526 compounds T141.1.1 to T141.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 142: This table discloses the 526 compounds T142.1.1 to T142.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 143: This table discloses the 526 compounds T143.1.1 to T143.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 144: This table discloses the 526 compounds T144.1.1 to T144.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 145: This table discloses the 526 compounds T145.1.1 to T145.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 146: This table discloses the 526 compounds T146.1.1 to T146.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 147: This table discloses the 526 compounds T147.1.1 to T147.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 148: This table discloses the 526 compounds T148.1.1 to T148.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 149: This table discloses the 526 compounds T149.1.1 to T149.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 150: This table discloses the 526 compounds T150.1.1 to T150.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Table 151: This table discloses the 526 compounds T151.1.1 to T151.1.526of the formula

in which, for each of these 526 specific compounds, each of thevariables R₁, R₂, R₅ and R₆ has the specific meaning given in thecorresponding line, appropriately selected from the 526 lines A.1.1 toA.1.526 of Table A.

Formulation examples for compounds of formula I:

Example F-1.1 to F-1.3 Emulsifiable Concentrates

Components F-1.1 F-1.2 F-1.3 compound of Tables 1 to 151 25% 40% 50%calcium dodecylbenzenesulfonate 5% 8% 6% castor oil polyethylene glycolether 5% — — (36 mol ethylenoxy units) tributylphenolpolyethylene glycolether — 12% 4% (30 mol ethylenoxy units) cyclohexanone — 15% 20% xylenemixture 65% 25% 20%

Emulsions of any desired concentration can be prepared by diluting suchconcentrates with water.

Example F-2 Emulsifiable Concentrate

Components F-2 compound of Tables 1 to 151 10% octylphenolpolyethyleneglycol ether 3% (4 to 5 mol ethylenoxy units) calciumdodecylbenzenesulfonate 3% castor oil polyglycol ether 4% (36 molethylenoxy units) cyclohexanone 30% xylene mixture 50%

Emulsions of any desired concentration can be prepared by diluting suchconcentrates with water.

Examples F-3.1 to F-3.4 Solutions

Components F-3.1 F-3.2 F-3.3 F-3.4 compound of Tables 1 to 151 80% 10%5% 95% propylene glycol monomethyl ether 20% — — — polyethylene glycol(relative molecular — 70% — — mass: 400 atomic mass units)N-methylpyrrolid-2-one — 20% — — epoxidised coconut oil — — 1% 5% benzin(boiling range: 160-190°) — — 94% —

The solutions are suitable for use in the form of microdrops.

Examples F-4.1 to F-4.4 Granulates

Components F-4.1 F-4.2 F-4.3 F-4.4 compound of Tables 1 to 151 5% 10% 8%21% kaolin 94% — 79% 54% highly dispersed silicic acid 1% — 13% 7%attapulgite — 90% — 18%

The novel compound is dissolved in dichloromethane, the solution issprayed onto the carrier and the solvent is then removed by distillationunder vacuum.

Examples F-5.1 and F-5.2 Dusts

Components F-5.1 F-5.2 compound of Tables 1 to 151 2% 5% highlydispersed silicic acid 1% 5% talcum 97% — kaolin — 90%

Ready for use dusts are obtained by intimately mixing all components.

Examples F-6.1 to F-6.3 Wettable Powders

Components F-6.1 F-6.2 F-6.3 compound of Tables 1 to 151 25% 50% 75%sodium lignin sulfonate 5% 5% — sodium lauryl sulfate 3% — 5% sodiumdiisobutylnaphthalene sulfonate — 6% 10% octylphenolpolyethylene glycolether — 2% — (7 to 8 mol ethylenoxy units) highly dispersed silicic acid5% 10% 10% kaolin 62% 27% —

All components are mixed and the mixture is thoroughly ground in asuitable mill to give wettable powders which can be diluted with waterto suspensions of any desired concentration.

Example F7 Flowable Concentrate for Seed Treatment

compound of Tables 1 to 151 40%  propylene glycol 5% copolymer butanolPO/EO 2% tristyrenephenole with 10-20 moles EO 2%1,2-benzisothiazolin-3-one (in the form of a 20% solution in 0.5%  water) monoazo-pigment calcium salt 5% Silicone oil (in the form of a75% emulsion in water) 0.2%   Water 45.3%  

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

The activity of the compositions according to the invention can bebroadened considerably, and adapted to prevailing circumstances, byadding other insecticidally, acaricidally and/or fungicidally activeingredients. The mixtures of the compounds of formula I with otherinsecticidally, acaricidally and/or fungicidally active ingredients mayalso have further surprising advantages which can also be described, ina wider sense, as synergistic activity. For example, better tolerance byplants, reduced phytotoxicity, insects can be controlled in theirdifferent development stages or better behaviour during theirproduction, for example during grinding or mixing, during their storageor during their use.

Suitable additions to active ingredients here are, for example,representatives of the following classes of active ingredients:organophosphorus compounds, nitrophenol derivatives, thioureas, juvenilehormones, formamidines, benzophenone derivatives, ureas, pyrrolederivatives, carbamates, pyrethroids, chlorinated hydrocarbons,acylureas, pyridyl-methyleneamino derivatives, macrolides,neonicotinoids and Bacillus thuringiensis preparations.

The following mixtures of the compounds of formula I with activeingredients are preferred (the abbreviation “TX” means “one compoundselected from the group consisting of the compounds of Table P and thecompounds represented by formulae T1 to T151 described in tables 1 to151 of the present invention”):

-   -   an adjuvant selected from the group of substances consisting of        petroleum oils (alternative name) (628)+TX,    -   an acaricide selected from the group of substances consisting of        1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,        2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts        name) (1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC        name) (1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name)        (981)+TX, abamectin (1)+TX, acequinocyl (3)+TX, acetoprole        [CCN]+TX, acrinathrin (9)+TX, aldicarb (16)+TX, aldoxycarb        (863)+TX, alpha-cypermethrin (202)+TX, amidithion (870)+TX,        amidoflumet [CCN]+TX, amidothioate (872)+TX, amiton (875)+TX,        amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, aramite        (881)+TX, arsenous oxide (882)+TX, AVI 382 (compound code)+TX,        AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,        azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX,        azocyclotin (46)+TX, azothoate (889)+TX, benomyl (62)+TX,        benoxafos (alternative name) [CCN]+TX, benzoximate (71)+TX,        benzyl benzoate (IUPAC name) [CCN]+TX, bifenazate (74)+TX,        bifenthrin (76)+TX, binapacryl (907)+TX, brofenvalerate        (alternative name)+TX, bromocyclen (918)+TX, bromophos (920)+TX,        bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin        (99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX,        butylpyridaben (alternative name)+TX, calcium polysulfide (IUPAC        name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX,        carbaryl (115)+TX, carbofuran (118)+TX, carbophenothion        (947)+TX, CGA 50′439 (development code) (125)+TX, chinomethionat        (126)+TX, chlorbenside (959)+TX, chlordimeform (964)+TX,        chlordimeform hydrochloride (964)+TX, chlorfenapyr (130)+TX,        chlorfenethol (968)+TX, chlorfenson (970)+TX, chlorfensulphide        (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate (975)+TX,        chloromebuform (977)+TX, chloromethiuron (978)+TX,        chloropropylate (983)+TX, chlorpyrifos (145)+TX,        chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, cinerin I        (696)+TX, cinerin II (696)+TX, cinerins (696)+TX, clofentezine        (158)+TX, closantel (alternative name) [CCN]+TX, coumaphos        (174)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos        (1010)+TX, cufraneb (1013)+TX, cyanthoate (1020)+TX,        cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin        (196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM        (1032)+TX, DDT (219)+TX, demephion (1037)+TX, demephion-O        (1037)+TX, demephion-S (1037)+TX, demeton (1038)+TX,        demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl        (224)+TX, demeton-S (1038)+TX, demeton-5-methyl (224)+TX,        demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,        dialifos (1042)+TX, diazinon (227)+TX, dichlofluanid (230)+TX,        dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicofol        (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX, dimefox        (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)        (653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton        (269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6        [CCN]+TX, dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon        (1097)+TX, dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl        sulfone (IUPAC name) (1103)+TX, disulfuram (alternative name)        [CCN]+TX, disulfoton (278)+TX, DNOC (282)+TX, dofenapyn        (1113)+TX, doramectin (alternative name) [CCN]+TX, endosulfan        (294)+TX, endothion (1121)+TX, EPN (297)+TX, eprinomectin        (alternative name) [CCN]+TX, ethion (309)+TX, ethoate-methyl        (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX, fenazaflor        (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,        fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad        (alternative name)+TX, fenpyroximate (345)+TX, fenson (1157)+TX,        fentrifanil (1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX,        fluacrypyrim (526)+TX, fluazuron (1166)+TX, flubenzimine        (1167)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX,        fluenetil (1169)+TX, flufenoxuron (370)+TX, flumethrin (372)+TX,        fluorbenside (1174)+TX, fluvalinate (1184)+TX, FMC 1137        (development code) (1185)+TX, formetanate (405)+TX, formetanate        hydrochloride (405)+TX, formothion (1192)+TX, formparanate        (1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox        (424)+TX, heptenophos (432)+TX, hexadecyl        cyclopropanecarboxylate (IUPAC/Chemical Abstracts name)        (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPAC name)        (542)+TX, isocarbophos (alternative name) (473)+TX, isopropyl        0-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,        ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,        jasmolin II (696)+TX, jodfenphos (1248)+TX, lindane (430)+TX,        lufenuron (490)+TX, malathion (492)+TX, malonoben (1254)+TX,        mecarbam (502)+TX, mephosfolan (1261)+TX, mesulfen (alternative        name) [CCN]+TX, methacrifos (1266)+TX, methamidophos (527)+TX,        methidathion (529)+TX, methiocarb (530)+TX, methomyl (531)+TX,        methyl bromide (537)+TX, metolcarb (550)+TX, mevinphos (556)+TX,        mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime        (alternative name) [CCN]+TX, mipafox (1293)+TX, monocrotophos        (561)+TX, morphothion (1300)+TX, moxidectin (alternative name)        [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-526        (compound code)+TX, nifluridide (1309)+TX, nikkomycins        (alternative name) [CCN]+TX, nitrilacarb (1526)+TX, nitrilacarb        1:1 zinc chloride complex (1526)+TX, NNI-0101 (compound        code)+TX, NNI-0250 (compound code)+TX, omethoate (594)+TX,        oxamyl (602)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX,        pp′-DDT (219)+TX, parathion (615)+TX, permethrin (626)+TX,        petroleum oils (alternative name) (628)+TX, phenkapton        (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone        (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon        (639)+TX, phoxim (642)+TX, pirimiphos-methyl (652)+TX,        polychloroterpenes (traditional name) (1347)+TX, polynactins        (alternative name) (653)+TX, proclonol (1350)+TX, profenofos        (662)+TX, promacyl (1354)+TX, propargite (671)+TX, propetamphos        (673)+TX, propoxur (678)+TX, prothidathion (1526)+TX, prothoate        (1362)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,        pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion        (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos        (711)+TX, quintiofos (1381)+TX, R-1492 (development code)        (1382)+TX, RA-17 (development code) (1383)+TX, rotenone        (722)+TX, schradan (1389)+TX, sebufos (alternative name)+TX,        selamectin (alternative name) [CCN]+TX, SI-0009 (compound        code)+TX, sophamide (1402)+TX, spirodiclofen (738)+TX,        spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,        sulfuram (alternative name) [CCN]+TX, sulfluramid (750)+TX,        sulfotep (753)+TX, sulfur (754)+TX, SZI-121 (development code)        (757)+TX, tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP        (1417)+TX, terbam (alternative name)+TX, tetrachlorvinphos        (777)+TX, tetradifon (786)+TX, tetranactin (alternative name)        (653)+TX, tetrasul (1425)+TX, thiafenox (alternative name)+TX,        thiocarboxime (1431)+TX, thiofanox (800)+TX, thiometon (801)+TX,        thioquinox (1436)+TX, thuringiensin (alternative name) [CCN]+TX,        triamiphos (1441)+TX, triarathene (1443)+TX, triazophos        (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,        trifenofos (1455)+TX, trinactin (alternative name) (653)+TX,        vamidothion (847)+TX, vaniliprole [CCN] and YI-5302 (compound        code)+TX,    -   an algicide selected from the group of substances consisting of        bethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX,        copper sulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX,        dichlorophen (232)+TX, endothal (295)+TX, fentin (347)+TX,        hydrated lime [CCN]+TX, nabam (566)+TX, quinoclamine (714)+TX,        quinonamid (1379)+TX, simazine (730)+TX, triphenyltin acetate        (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name)        (347)+TX,    -   an anthelmintic selected from the group of substances consisting        of abamectin (1)+TX, crufomate (1011)+TX, doramectin        (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin        benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,        ivermectin (alternative name) [CCN]+TX, milbemycin oxime        (alternative name) [CCN]+TX, moxidectin (alternative name)        [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)        [CCN]+TX, spinosad (737) and thiophanate (1435)+TX,    -   an avicide selected from the group of substances consisting of        chloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,        pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,    -   a bactericide selected from the group of substances consisting        of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,        4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name)        (748)+TX, 8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX,        copper dioctanoate (IUPAC name) (170)+TX, copper hydroxide        (IUPAC name) (169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX,        dipyrithione (1105)+TX, dodicin (1112)+TX, fenaminosulf        (1144)+TX, formaldehyde (404)+TX, hydrargaphen (alternative        name) [CCN]+TX, kasugamycin (483)+TX, kasugamycin hydrochloride        hydrate (483)+TX, nickel bis(dimethyldithiocarbamate) (IUPAC        name) (1308)+TX, nitrapyrin (580)+TX, octhilinone (590)+TX,        oxolinic acid (606)+TX, oxytetracycline (611)+TX, potassium        hydroxyquinoline sulfate (446)+TX, probenazole (658)+TX,        streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,        tecloftalam (766)+TX, and thiomersal (alternative name)        [CCN]+TX,    -   a biological agent selected from the group of substances        consisting of Adoxophyes orana GV (alternative name) (12)+TX,        Agrobacterium radiobacter (alternative name) (13)+TX, Amblyseius        spp. (alternative name) (19)+TX, Anagrapha falcifera NPV        (alternative name) (28)+TX, Anagrus atomus (alternative name)        (29)+TX, Aphelinus abdominalis (alternative name) (33)+TX,        Aphidius colemani (alternative name) (34)+TX, Aphidoletes        aphidimyza (alternative name) (35)+TX, Autographa californica        NPV (alternative name) (38)+TX, Bacillus firmus (alternative        name) (48)+TX, Bacillus sphaericus Neide (scientific name)        (49)+TX, Bacillus thuringiensis Berliner (scientific name)        (51)+TX, Bacillus thuringiensis subsp. aizawai (scientific name)        (51)+TX, Bacillus thuringiensis subsp. israelensis (scientific        name) (51)+TX, Bacillus thuringiensis subsp. japonensis        (scientific name) (51)+TX, Bacillus thuringiensis subsp.        kurstaki (scientific name) (51)+TX, Bacillus thuringiensis        subsp. tenebrionis (scientific name) (51)+TX, Beauveria bassiana        (alternative name) (53)+TX, Beauveria brongniartii (alternative        name) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,        Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia        pomonella GV (alternative name) (191)+TX, Dacnusa sibirica        (alternative name) (212)+TX, Diglyphus isaea (alternative name)        (254)+TX, Encarsia formosa (scientific name) (293)+TX,        Eretmocerus eremicus (alternative name) (300)+TX, Helicoverpa        zea NPV (alternative name) (431)+TX, Heterorhabditis        bacteriophora and H. megidis (alternative name) (433)+TX,        Hippodamia convergens (alternative name) (442)+TX, Leptomastix        dactylopii (alternative name) (488)+TX, Macrolophus caliginosus        (alternative name) (491)+TX, Mamestra brassicae NPV (alternative        name) (494)+TX, Metaphycus helvolus (alternative name) (522)+TX,        Metarhizium anisopliae var. acridum (scientific name) (523)+TX,        Metarhizium anisopliae var. anisopliae (scientific name)        (523)+TX, Neodiprion sertifer NPV and N. lecontei NPV        (alternative name) (575)+TX, Orius spp. (alternative name)        (596)+TX, Paecilomyces fumosoroseus (alternative name) (613)+TX,        Phytoseiulus persimilis (alternative name) (644)+TX, Spodoptera        exigua multicapsid nuclear polyhedrosis virus (scientific name)        (741)+TX, Steinemema bibionis (alternative name) (742)+TX,        Steinemema carpocapsae (alternative name) (742)+TX, Steinemema        feltiae (alternative name) (742)+TX, Steinemema glaseri        (alternative name) (742)+TX, Steinemema riobrave (alternative        name) (742)+TX, Steinemema riobravis (alternative name)        (742)+TX, Steinemema scapterisci (alternative name) (742)+TX,        Steinemema spp. (alternative name) (742)+TX, Trichogramma spp.        (alternative name) (826)+TX, Typhlodromus occidentalis        (alternative name) (844) and Verticillium lecanii (alternative        name) (848)+TX,    -   a soil sterilant selected from the group of substances        consisting of iodomethane (IUPAC name) (542) and methyl bromide        (537)+TX,    -   a chemosterilant selected from the group of substances        consisting of apholate [CCN]+TX, bisazir (alternative name)        [CCN]+TX, busulfan (alternative name) [CCN]+TX, diflubenzuron        (250)+TX, dimatif (alternative name) [CCN]+TX, hemel [CCN]+TX,        hempa [CCN]+TX, metepa [CCN]+TX, methiotepa [CCN]+TX, methyl        apholate [CCN]+TX, morzid [CCN]+TX, penfluoron (alternative        name) [CCN]+TX, tepa [CCN]+TX, thiohempa (alternative name)        [CCN]+TX, thiotepa (alternative name) [CCN]+TX, tretamine        (alternative name) [CCN] and uredepa (alternative name)        [CCN]+TX,    -   an insect pheromone selected from the group of substances        consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol        (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate (IUPAC name)        (829)+TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,        (E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,        (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX,        (Z)-hexadec-11-enal (IUPAC name) (436)+TX,        (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437)+TX,        (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,        (Z)-icos-13-en-10-one (IUPAC name) (448)+TX,        (Z)-tetradec-7-en-1-al (IUPAC name) (782)+TX,        (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,        (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,        (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,        (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,        (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,        14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol        with 4-methylnonan-5-one (IUPAC name) (544)+TX,        alpha-multistriatin (alternative name) [CCN]+TX, brevicomin        (alternative name) [CCN]+TX, codlelure (alternative name)        [CCN]+TX, codlemone (alternative name) (167)+TX, cuelure        (alternative name) (179)+TX, disparlure (277)+TX,        dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl        acetate (IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate        (IUPAC name) (284)+TX, dominicalure (alternative name) [CCN]+TX,        ethyl 4-methyloctanoate (IUPAC name) (317)+TX, eugenol        (alternative name) [CCN]+TX, frontalin (alternative name)        [CCN]+TX, gossyplure (alternative name) (420)+TX, grandlure        (421)+TX, grandlure I (alternative name) (421)+TX, grandlure II        (alternative name) (421)+TX, grandlure III (alternative name)        (421)+TX, grandlure IV (alternative name) (421)+TX, hexylure        [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol        (alternative name) [CCN]+TX, japonilure (alternative name)        (481)+TX, lineatin (alternative name) [CCN]+TX, litlure        (alternative name) [CCN]+TX, looplure (alternative name)        [CCN]+TX, medlure [CCN]+TX, megatomoic acid (alternative name)        [CCN]+TX, methyl eugenol (alternative name) (526)+TX, muscalure        (563)+TX, octadeca-2,13-dien-1-yl acetate (IUPAC name) (588)+TX,        octadeca-3,13-dien-1-yl acetate (IUPAC name) (589)+TX, orfralure        (alternative name) [CCN]+TX, oryctalure (alternative name)        (317)+TX, ostramone (alternative name) [CCN]+TX, siglure        [CCN]+TX, sordidin (alternative name) (736)+TX, sulcatol        (alternative name) [CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC        name) (785)+TX, trimedlure (839)+TX, trimedlure A (alternative        name) (839)+TX, trimedlure B₁ (alternative name) (839)+TX,        trimedlure B₂ (alternative name) (839)+TX, trimedlure C        (alternative name) (839) and trunc-call (alternative name)        [CCN]+TX,    -   an insect repellent selected from the group of substances        consisting of 2-(octylthio)-ethanol (IUPAC name) (591)+TX,        butopyronoxyl (933)+TX, butoxy(polypropylene glycol) (936)+TX,        dibutyl adipate (IUPAC name) (1046)+TX, dibutyl phthalate        (1047)+TX, dibutyl succinate (IUPAC name) (1048)+TX,        diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX, dimethyl        phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide        [CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide        [CCN]+TX, oxamate [CCN] and picaridin [CCN]+TX,    -   an insecticide selected from the group of substances consisting        of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name)        (1058)+TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC        name) (1056), +TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts        name) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene        (IUPAC name) (1063)+TX, 1-bromo-2-chloroethane (IUPAC/Chemical        Abstracts name) (916)+TX,        2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)        (1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl        phosphate (IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl        dimethylcarbamate (IUPAC/Chemical Abstracts name) (1109)+TX,        2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts        name) (935)+TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl        methylcarbamate (IUPAC/Chemical Abstracts name) (1084)+TX,        2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986)+TX,        2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,        2-imidazolidone (IUPAC name) (1225)+TX,        2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,        2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name)        (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433)+TX,        3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,        3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name)        (1283)+TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate        (IUPAC name) (1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl        dimethylcarbamate (IUPAC name) (1085)+TX, abamectin (1)+TX,        acephate (2)+TX, acetamiprid (4)+TX, acethion (alternative name)        [CCN]+TX, acetoprole [CCN]+TX, acrinathrin (9)+TX, acrylonitrile        (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb (16)+TX,        aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,        allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,        alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name)        [CCN]+TX, aluminium phosphide (640)+TX, amidithion (870)+TX,        amidothioate (872)+TX, aminocarb (873)+TX, amiton (875)+TX,        amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, anabasine        (877)+TX, athidathion (883)+TX, AVI 382 (compound code)+TX, AZ        60541 (compound code)+TX, azadirachtin (alternative name)        (41)+TX, azamethiphos (42)+TX, azinphos-ethyl (44)+TX,        azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillus        thuringiensis delta endotoxins (alternative name) (52)+TX,        barium hexafluorosilicate (alternative name) [CCN]+TX, barium        polysulfide (IUPAC/Chemical Abstracts name) (892)+TX, barthrin        [CCN]+TX, Bayer 22/190 (development code) (893)+TX, Bayer 22408        (development code) (894)+TX, bendiocarb (58)+TX, benfuracarb        (60)+TX, bensultap (66)+TX, beta-cyfluthrin (194)+TX,        beta-cypermethrin (203)+TX, bifenthrin (76)+TX, bioallethrin        (78)+TX, bioallethrin S-cyclopentenyl isomer (alternative name)        (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin (908)+TX,        bioresmethrin (80)+TX, bis(2-chloroethyl)ether (IUPAC name)        (909)+TX, bistrifluoron (83)+TX, borax (86)+TX, brofenvalerate        (alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen        (918)+TX, bromo-DDT (alternative name) [CCN]+TX, bromophos        (920)+TX, bromophos-ethyl (921)+TX, bufencarb (924)+TX,        buprofezin (99)+TX, butacarb (926)+TX, butathiofos (927)+TX,        butocarboxim (103)+TX, butonate (932)+TX, butoxycarboxim        (104)+TX, butylpyridaben (alternative name)+TX, cadusafos        (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,        calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,        carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX,        carbon disulfide (IUPAC/Chemical Abstracts name) (945)+TX,        carbon tetrachloride (IUPAC name) (946)+TX, carbophenothion        (947)+TX, carbosulfan (119)+TX, cartap (123)+TX, cartap        hydrochloride (123)+TX, cevadine (alternative name) (725)+TX,        chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone        (963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride        (964)+TX, chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX,        chlorfenvinphos (131)+TX, chlorfluazuron (132)+TX, chlormephos        (136)+TX, chloroform [CCN]+TX, chloropicrin (141)+TX,        chlorphoxim (989)+TX, chlorprazophos (990)+TX, chlorpyrifos        (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX,        chromafenozide (150)+TX, cinerin I (696)+TX, cinerin II        (696)+TX, cinerins (696)+TX, cis-resmethrin (alternative        name)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,        cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,        clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper        arsenate [CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX,        coumithoate (1006)+TX, crotamiton (alternative name) [CCN]+TX,        crotoxyphos (1010)+TX, crufomate (1011)+TX, cryolite        (alternative name) (177)+TX, CS 708 (development code)        (1012)+TX, cyanofenphos (1019)+TX, cyanophos (184)+TX,        cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin        (188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX,        cypermethrin (201)+TX, cyphenothrin (206)+TX, cyromazine        (209)+TX, cythioate (alternative name) [CCN]+TX, d-limonene        (alternative name) [CCN]+TX, d-tetramethrin (alternative name)        (788)+TX, DAEP (1031)+TX, dazomet (216)+TX, DDT (219)+TX,        decarbofuran (1034)+TX, deltamethrin (223)+TX, demephion        (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX, demeton        (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX,        demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-5-methyl        (224)+TX, demeton-5-methylsulphon (1039)+TX, diafenthiuron        (226)+TX, dialifos (1042)+TX, diamidafos (1044)+TX, diazinon        (227)+TX, dicapthon (1050)+TX, dichlofenthion (1051)+TX,        dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicresyl        (alternative name) [CCN]+TX, dicrotophos (243)+TX, dicyclanil        (244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl        phosphate (IUPAC name) (1076)+TX, diflubenzuron (250)+TX, dilor        (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX, dimefox        (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin        (1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex        (1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX,        dinosam (1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX,        diofenolan (1099)+TX, dioxabenzofos (1100)+TX, dioxacarb        (1101)+TX, dioxathion (1102)+TX, disulfoton (278)+TX,        dithicrofos (1108)+TX, DNOC (282)+TX, doramectin (alternative        name) [CCN]+TX, DSP (1115)+TX, ecdysterone (alternative name)        [CCN]+TX, EI 1642 (development code) (1118)+TX, emamectin        (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,        empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX,        endrin (1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane        (1124)+TX, eprinomectin (alternative name) [CCN]+TX,        esfenvalerate (302)+TX, etaphos (alternative name) [CCN]+TX,        ethiofencarb (308)+TX, ethion (309)+TX, ethiprole (310)+TX,        ethoate-methyl (1134)+TX, ethoprophos (312)+TX, ethyl formate        (IUPAC name) [CCN]+TX, ethyl-DDD (alternative name) (1056)+TX,        ethylene dibromide (316)+TX, ethylene dichloride (chemical name)        (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,        etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos        (326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX,        fenethacarb (1149)+TX, fenfluthrin (1150)+TX, fenitrothion        (335)+TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb        (340)+TX, fenpirithrin (1155)+TX, fenpropathrin (342)+TX,        fenpyrad (alternative name)+TX, fensulfothion (1158)+TX,        fenthion (346)+TX, fenthion-ethyl [CCN]+TX, fenvalerate        (349)+TX, fipronil (354)+TX, flonicamid (358)+TX, flubendiamide        (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,        flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil        (1169)+TX, flufenerim [CCN]+TX, flufenoxuron (370)+TX,        flufenprox (1171)+TX, flumethrin (372)+TX, fluvalinate        (1184)+TX, FMC 1137 (development code) (1185)+TX, fonofos        (1191)+TX, formetanate (405)+TX, formetanate hydrochloride        (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,        fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate        (408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin        (1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX,        guazatine (422)+TX, guazatine acetates (422)+TX, GY-81        (development code) (423)+TX, halfenprox (424)+TX, halofenozide        (425)+TX, HCH (430)+TX, HEOD (1070)+TX, heptachlor (1211)+TX,        heptenophos (432)+TX, heterophos [CCN]+TX, hexaflumuron        (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX, hydrogen        cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,        imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb        (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX,        isazofos (1231)+TX, isobenzan (1232)+TX, isocarbophos        (alternative name) (473)+TX, isodrin (1235)+TX, isofenphos        (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX, isopropyl        O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,        isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion        (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I        (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile        hormone I (alternative name) [CCN]+TX, juvenile hormone II        (alternative name) [CCN]+TX, juvenile hormone III (alternative        name) [CCN]+TX, kelevan (1249)+TX, kinoprene (484)+TX,        lambda-cyhalothrin (198)+TX, lead arsenate [CCN]+TX, lepimectin        (CCN)+TX, leptophos (1250)+TX, lindane (430)+TX, lirimfos        (1251)+TX, lufenuron (490)+TX, lythidathion (1253)+TX, m-cumenyl        methylcarbamate (IUPAC name) (1014)+TX, magnesium phosphide        (IUPAC name) (640)+TX, malathion (492)+TX, malonoben (1254)+TX,        mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,        menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride        (513)+TX, mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam        (519)+TX, metam-potassium (alternative name) (519)+TX,        metam-sodium (519)+TX, methacrifos (1266)+TX, methamidophos        (527)+TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts        name) (1268)+TX, methidathion (529)+TX, methiocarb (530)+TX,        methocrotophos (1273)+TX, methomyl (531)+TX, methoprene        (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternative        name) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX,        methyl bromide (537)+TX, methyl isothiocyanate (543)+TX,        methylchloroform (alternative name) [CCN]+TX, methylene chloride        [CCN]+TX, metofluthrin [CCN]+TX, metolcarb (550)+TX,        metoxadiazone (1288)+TX, mevinphos (556)+TX, mexacarbate        (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative        name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,        monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin        (alternative name) [CCN]+TX, naftalofos (alternative name)        [CCN]+TX, naled (567)+TX, naphthalene (IUPAC/Chemical Abstracts        name) (1303)+TX, NC-170 (development code) (1306)+TX, NC-184        (compound code)+TX, nicotine (578)+TX, nicotine sulfate        (578)+TX, nifluridide (1309)+TX, nitenpyram (579)+TX, nithiazine        (1311)+TX, nitrilacarb (1526)+TX, nitrilacarb 1:1 zinc chloride        complex (1526)+TX, NNI-0101 (compound code)+TX, NNI-0250        (compound code)+TX, nornicotine (traditional name) (1319)+TX,        novaluron (585)+TX, noviflumuron (586)+TX,        O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC        name) (1057)+TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl        phosphorothioate (IUPAC name) (1074)+TX, O,O-diethyl        O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name)        (1075)+TX, O,O,O′,O′-tetrapropyl dithiopyrophosphate (IUPAC        name) (1424)+TX, oleic acid (IUPAC name) (593)+TX, omethoate        (594)+TX, oxamyl (602)+TX, oxydemeton-methyl (609)+TX,        oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT        (219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,        parathion-methyl (616)+TX, penfluoron (alternative name)        [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate        (IUPAC name) (623)+TX, permethrin (626)+TX, petroleum oils        (alternative name) (628)+TX, PH 60-38 (development code)        (1328)+TX, phenkapton (1330)+TX, phenothrin (630)+TX, phenthoate        (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan        (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidon        (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,        phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb        (651)+TX, pirimiphos-ethyl (1345)+TX, pirimiphos-methyl        (652)+TX, polychlorodicyclopentadiene isomers (IUPAC name)        (1346)+TX, polychloroterpenes (traditional name) (1347)+TX,        potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX,        prallethrin (655)+TX, precocene I (alternative name) [CCN]+TX,        precocene II (alternative name) [CCN]+TX, precocene III        (alternative name) [CCN]+TX, primidophos (1349)+TX, profenofos        (662)+TX, profluthrin [CCN]+TX, promacyl (1354)+TX, promecarb        (1355)+TX, propaphos (1356)+TX, propetamphos (673)+TX, propoxur        (678)+TX, prothidathion (1526)+TX, prothiofos (686)+TX,        prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine        (688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin        (1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,        pyrethrins (696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX,        pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate        (1370)+TX, pyriproxyfen (708)+TX, quassia (alternative name)        [CCN]+TX, quinalphos (711)+TX, quinalphos-methyl (1376)+TX,        quinothion (1380)+TX, quintiofos (1381)+TX, R-1492 (development        code) (1382)+TX, rafoxanide (alternative name) [CCN]+TX,        resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (development        code) (723)+TX, RU 25475 (development code) (1386)+TX, ryania        (alternative name) (1387)+TX, ryanodine (traditional name)        (1387)+TX, sabadilla (alternative name) (725)+TX, schradan        (1389)+TX, sebufos (alternative name)+TX, selamectin        (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, SI-0205        (compound code)+TX, SI-0404 (compound code)+TX, SI-0405        (compound code)+TX, silafluofen (728)+TX, SN 72129 (development        code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide        (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name)        (1399)+TX, sodium hexafluorosilicate (1400)+TX, sodium        pentachlorophenoxide (623)+TX, sodium selenate (IUPAC name)        (1401)+TX, sodium thiocyanate [CCN]+TX, sophamide (1402)+TX,        spinosad (737)+TX, spiromesifen (739)+TX, spirotetrmat (CCN)+TX,        sulcofuron (746)+TX, sulcofuron-sodium (746)+TX, sulfluramid        (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX,        sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,        tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,        tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos        (764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos        (770)+TX, TEPP (1417)+TX, terallethrin (1418)+TX, terbam        (alternative name)+TX, terbufos (773)+TX, tetrachloroethane        [CCN]+TX, tetrachlorvinphos (777)+TX, tetramethrin (787)+TX,        theta-cypermethrin (204)+TX, thiacloprid (791)+TX, thiafenox        (alternative name)+TX, thiamethoxam (792)+TX, thicrofos        (1428)+TX, thiocarboxime (1431)+TX, thiocyclam (798)+TX,        thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,        thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX,        thiosultap (803)+TX, thiosultap-sodium (803)+TX, thuringiensin        (alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrin        (812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX,        triamiphos (1441)+TX, triazamate (818)+TX, triazophos (820)+TX,        triazuron (alternative name)+TX, trichlorfon (824)+TX,        trichlormetaphos-3 (alternative name) [CCN]+TX, trichloronat        (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,        trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,        vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX,        veratrine (alternative name) (725)+TX, XMC (853)+TX, xylylcarb        (854)+TX, YI-5302 (compound code)+TX, zeta-cypermethrin        (205)+TX, zetamethrin (alternative name)+TX, zinc phosphide        (640)+TX, zolaprofos (1469) and ZXI 8901 (development code)        (858)+TX,    -   a molluscicide selected from the group of substances consisting        of bis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide        [CCN]+TX, calcium arsenate [CCN]+TX, cloethocarb (999)+TX,        copper acetoarsenite [CCN]+TX, copper sulfate (172)+TX, fentin        (347)+TX, ferric phosphate (IUPAC name) (352)+TX, metaldehyde        (518)+TX, methiocarb (530)+TX, niclosamide (576)+TX,        niclosamide-olamine (576)+TX, pentachlorophenol (623)+TX, sodium        pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX, thiodicarb        (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,        trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347)        and triphenyltin hydroxide (IUPAC name) (347)+TX,    -   a nematicide selected from the group of substances consisting of        AKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane        (IUPAC/Chemical Abstracts name) (1045)+TX, 1,2-dichloropropane        (IUPAC/Chemical Abstracts name) (1062)+TX, 1,2-dichloropropane        with 1,3-dichloropropene (IUPAC name) (1063)+TX,        1,3-dichloropropene (233)+TX, 3,4-dichlorotetrahydrothiophene        1,1-dioxide (IUPAC/Chemical Abstracts name) (1065)+TX,        3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980)+TX,        5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC        name) (1286)+TX, 6-isopentenylaminopurine (alternative name)        (210)+TX, abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb        (15)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, AZ 60541        (compound code)+TX, benclothiaz [CCN]+TX, benomyl (62)+TX,        butylpyridaben (alternative name)+TX, cadusafos (109)+TX,        carbofuran (118)+TX, carbon disulfide (945)+TX, carbosulfan        (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX,        cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX,        dazomet (216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos        (1044)+TX, dichlofenthion (1051)+TX, dicliphos (alternative        name)+TX, dimethoate (262)+TX, doramectin (alternative name)        [CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX,        eprinomectin (alternative name) [CCN]+TX, ethoprophos (312)+TX,        ethylene dibromide (316)+TX, fenamiphos (326)+TX, fenpyrad        (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate        (408)+TX, fosthietan (1196)+TX, furfural (alternative name)        [CCN]+TX, GY-81 (development code) (423)+TX, heterophos        [CCN]+TX, iodomethane (IUPAC name) (542)+TX, isamidofos        (1230)+TX, isazofos (1231)+TX, ivermectin (alternative name)        [CCN]+TX, kinetin (alternative name) (210)+TX, mecarphon        (1258)+TX, metam (519)+TX, metam-potassium (alternative name)        (519)+TX, metam-sodium (519)+TX, methyl bromide (537)+TX, methyl        isothiocyanate (543)+TX, milbemycin oxime (alternative name)        [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrothecium        verrucaria composition (alternative name) (565)+TX, NC-184        (compound code)+TX, oxamyl (602)+TX, phorate (636)+TX,        phosphamidon (639)+TX, phosphocarb [CCN]+TX, sebufos        (alternative name)+TX, selamectin (alternative name) [CCN]+TX,        spinosad (737)+TX, terbam (alternative name)+TX, terbufos        (773)+TX, tetrachlorothiophene (IUPAC/Chemical Abstracts name)        (1422)+TX, thiafenox (alternative name)+TX, thionazin (1434)+TX,        triazophos (820)+TX, triazuron (alternative name)+TX, xylenols        [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name)        (210)+TX,    -   a nitrification inhibitor selected from the group of substances        consisting of potassium ethylxanthate [CCN] and nitrapyrin        (580)+TX,    -   a plant activator selected from the group of substances        consisting of acibenzolar (6)+TX, acibenzolar-5-methyl (6)+TX,        probenazole (658) and Reynoutria sachalinensis extract        (alternative name) (720)+TX,    -   a rodenticide selected from the group of substances consisting        of 2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,        4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name)        (748)+TX, alpha-chlorohydrin [CCN]+TX, aluminium phosphide        (640)+TX, antu (880)+TX, arsenous oxide (882)+TX, barium        carbonate (891)+TX, bisthiosemi (912)+TX, brodifacoum (89)+TX,        bromadiolone (91)+TX, bromethalin (92)+TX, calcium cyanide        (444)+TX, chloralose (127)+TX, chlorophacinone (140)+TX,        cholecalciferol (alternative name) (850)+TX, coumachlor        (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,        crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,        diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen        (357)+TX, fluoroacetamide (379)+TX, flupropadine (1183)+TX,        flupropadine hydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH        (430)+TX, hydrogen cyanide (444)+TX, iodomethane (IUPAC name)        (542)+TX, lindane (430)+TX, magnesium phosphide (IUPAC name)        (640)+TX, methyl bromide (537)+TX, norbormide (1318)+TX,        phosacetim (1336)+TX, phosphine (IUPAC name) (640)+TX,        phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite        [CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium        arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate        (735)+TX, strychnine (745)+TX, thallium sulfate [CCN]+TX,        warfarin (851) and zinc phosphide (640)+TX,    -   a synergist selected from the group of substances consisting of        2-(2-butoxyethoxy)-ethyl piperonylate (IUPAC name) (934)+TX,        5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name)        (903)+TX, farnesol with nerolidol (alternative name) (324)+TX,        MB-599 (development code) (498)+TX, MGK 264 (development code)        (296)+TX, piperonyl butoxide (649)+TX, piprotal (1343)+TX,        propyl isomer (1358)+TX, S421 (development code) (724)+TX,        sesamex (1393)+TX, sesasmolin (1394) and sulfoxide (1406)+TX,    -   an animal repellent selected from the group of substances        consisting of anthraquinone (32)+TX, chloralose (127)+TX, copper        naphthenate [CCN]+TX, copper oxychloride (171)+TX, diazinon        (227)+TX, dicyclopentadiene (chemical name) (1069)+TX, guazatine        (422)+TX, guazatine acetates (422)+TX, methiocarb (530)+TX,        pyridin-4-amine (IUPAC name) (23)+TX, thiram (804)+TX,        trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram        (856)+TX,    -   a virucide selected from the group of substances consisting of        imanin (alternative name) [CCN] and ribavirin (alternative name)        [CCN]+TX,    -   a wound protectant selected from the group of substances        consisting of mercuric oxide (526)+TX, octhilinone (590) and        thiophanate-methyl (802)+TX, an insecticide selected from the        group consisting of the compound of

and biologically active compounds selected from the group consisting ofglyphosate [1071-83-6] and its salts (diammonium [69254-40-6])isopropylammonium [38641-94-0],monoammonium [40465-66-5], potassium[70901-20-1], sesquisodium [70393-85-0], trimesium [81591-81-3]),glufosinate [52676-47-2] and its salts (e.g. ammonium [77182-82-2],azaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole[116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole[119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole[106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole[136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol[76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX,imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole[125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate[101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole[178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX,propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX,tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX,triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole[99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol[12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX,bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX,fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph[81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim[110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil[74738-17-3]+TX, fludioxonil [152641-86-1]+TX, benalaxyl[71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX,R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl[77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX,debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole[148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline[24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX,procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid[188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX,flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin[5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide[130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3][112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin[131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc.BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin[361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin[133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin[248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin[175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb[12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX,thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX,captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid[1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX,tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX,copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX,coppersulfate [7758-98-7]+TX, copperoxide [1317-39-1]+TX, mancopper[53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX,nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX,iprobenphos [26087-47-8]+TX, isoprothiolane [50526-35-1]+TX, phosdiphen[36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl[57018-04-9]+TX, acibenzolar-5-methyl [135158-54-2]+TX, anilazine[101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX,chlorothalonil [1897-45-6]+TX, cyflufenamid [526409-60-3]+TX, cymoxanil[57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX,diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb[87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-L190 (flumorph)[211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX,etridiazole [2593-15-9]+TX, famoxadone [135267-57-3]+TX, fenamidone[161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX,ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide[239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol[10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (cyazofamid)[120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX,probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid[189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen[124495-18-7]+TX, quintozene [82-68-8]+TX, sulfur [7704-34-9]+TX,tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole[41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX,zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX, thecompound of formula F-1

wherein Ra₅ is trifluoromethyl or difluoromethyl (WO2004/058723)+TX, thecompound of formula F-2

wherein Ra_(b) is trifluoromethyl or difluoromethyl (WO2004/058723)+TX,the racemic compound of formula F-3 (syn)

wherein Ra₇ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, theracemic mixture of formula F-4 (anti)

wherein Ra₇ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, thecompound of formula F-5

which is an epimeric mixture of racemic compounds of formulae F-3 (syn)and F-4 (anti),

wherein the ratio from racemic compounds of formula F-3 (syn) to racemiccompounds of formula F-4 (anti) is from 1000:1 to 1:1000 and wherein Ra₇is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, the compound offormula F-6

wherein Ra₈ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, theracemic compound of formula F-7 (trans)

wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, theracemic compound of formula F-8 (cis)

wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, thecompound of formula F-9

which is a mixture of the racemic compounds of formulae F-7 (trans) andF-8 (cis), wherein the ratio of the racemic compound of formula F-7(trans) to the racemic compound of formula F-8 (cis) is 2:1 to 100:1;and wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX,the compound of formula F-10

wherein R₁₀ is trifluoromethyl or difluoromethyl (WO2004/058723)+TX, theracemic compound of formula F-11 (trans)

wherein R₁₁ is trifluoromethyl or difluoromethyl (WO 03/074491)+TX, theracemic compound of formula F-12 (cis)

wherein R₁₁ is trifluoromethyl or difluoromethyl (WO 03/074491)+TX, thecompound of formula F-13

which is a racemic mixture of formulae F-11 (trans) and F-12 (cis), andwherein R₁₁ is trifluoromethyl or difluoromethyl (WO 03/074491)+TX, thecompound of formula F-14

(WO 2004/058723)+TX, and the compound of formula F-15

+TX.

The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. Thecompounds of the formulae A-1 to A-26 are described in WO 03/015518 orin WO 04/067528.The above described mixing partners are known. Where theactive ingredients are included in “The Pesticide Manual” [The PesticideManual—A World Compendium; Thirteenth Edition; Editor: C. D. S. Tomlin;The British Crop Protection Council], they are described therein underthe entry number given in round brackets hereinabove for the particularcompound; for example, the compound “abamectin” is described under entrynumber (1). Where “[CCN]” is added hereinabove to the particularcompound, the compound in question is included in the “Compendium ofPesticide Common Names”, which is accessible on the internet [A. Wood;Compendium of Pesticide Common Names, Copyright © 1995-2004]; forexample, the compound “acetoprole” is described under the internetaddress http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “development code”is used or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The active ingredient mixture of the compounds of formula I selectedfrom tables T1 to T151 with active ingredients described above comprisesa compound selected from tables T1 to T151 and an active ingredient asdescribed above preferably in a mixing ratio of from 100:1 to 1:6000,especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to1:20, even more especially from 10:1 to 1:10, very especially from 5:1and 1:5, special preference being given to a ratio of from 2:1 to 1:2,and a ratio of from 4:1 to 2:1 being likewise preferred, above all in aratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.Those mixing ratios are understood to include, on the one hand, ratiosby weight and also, on other hand, molar ratios.

The mixtures comprising a compound of formula I selected from tables T1to T151 and one or more active ingredients as described above can beapplied, for example, in a single “ready-mix” form, in a combined spraymixture composed from separate formulations of the single activeingredient components, such as a “tank-mix”, and in a combined use ofthe single active ingredients when applied in a sequential manner, i.e.one after the other with a reasonably short period, such as a few hoursor days. The order of applying the compounds of formula I selected fromtables T1 to T151 and the active ingredients as described above is notessential for working the present invention.

BIOLOGICAL EXAMPLES Fungicidal Action Example B-1 Plasmopara viticola:Downy Mildew of Grapevine, Preventative Test

Plasmopara viticola (downy mildew of grapevine): Grape vine leaf disksare placed on agar in multiwell plates (24-well format) and sprayed withthe formulated (2% Dimethylsulfoxid, 0.025% Tween 20) test solutions.After drying, the leaf disks are inoculated with a spore suspension ofthe fungus (80′000 conidia/ml). After appropriate incubation, thepreventive fungicidal activity of a compound is assessed 6 days afterinoculation as disease damage on the leaf disks and calculated aspercent efficacy relative to untreated infected control. (0=no controlof Plasmopara viticola, 100% complete control). In this test, compoundslisted in Table P above show good activity. In particular compound P.10shows an activity of at least 50% at an application rate of 200 ppm.

Example B-2 Botrytis cinerea: Gray Mould, Preventative Test

Botrytis cinerea (Gray mould): Bean leaf disks are placed on agar inmultiwell plates (24-well format) and sprayed with the formulated (2%Dimethylsulfoxid, 0.025% Tween 20) test solutions. After drying, theleaf disks are inoculated with a spore suspension of the fungus (60′000conidia/ml). After appropriate incubation, the preventive fungicidalactivity of a compound is assessed 3 days after inoculation as diseasedamage on the leaf disks and calculated as percent efficacy relative tountreated infected control. (0=no control of Botrytis cinerea,100%=complete control). In this test, compounds listed in Table P aboveshow good activity. In particular compound P.29 shows an activity of atleast 50% at an application rate of 200 ppm.

Example B-3 Erysiphe graminis f.sp. tritici: Wheat Powdery Mildew,Preventative Test

Erysiphe graminis f.sp. tritici (Wheat powdery mildew): Wheat leafsegments are placed on agar in multiwell plates (24-well format) andsprayed with the formulated (2% Dimethylsulfoxid, 0.025% Tween 20) testsolutions. After drying, the leaf disks are inoculated with spores ofthe fungus (50 conidia/mm2). After appropriate incubation, thepreventive fungicidal activity of a compound is assessed 7 days afterinoculation as disease damage on the leaf disks and calculated aspercent efficacy relative to untreated infected control. (0=no controlof Erysiphe graminis f.sp. tritici, 100%=complete control). In thistest, compounds listed in Table P above show good activity. Inparticular compounds P.07, P.09, P.21, P.22, P.26, P.28, P.29, P.30,P.35, P.59, P.61, P.62, P.63, P.64, P.68, P.69, P.73, P.76, P.77, P.78and P.82 show an activity of at least 50% at an application rate of 200ppm.

Example B-4 Erysiphe graminis f.sp. hordei: Powdery Mildew of Barley,Curative Test

Erysiphe graminis f.sp. hordei (Barley powdery mildew): Barley leafsegments are placed on agar in multiwell plates (24-well format). Theleaf disks are inoculated with spores of the fungus (120 conidia/mm2).After 24 h the leaf disks are sprayed with the formulated (2%Dimethylsulfoxid, 0.025% Tween 20) test solutions. After appropriateincubation, the curative fungicidal activity of a compound is assessed 7days after inoculation as disease damage on the leaf disks andcalculated as percent efficacy relative to untreated infected control(0=no control of Erysiphe graminis f.sp. hordei, 100%=complete control).In this test, compounds listed in Table P above show good activity. Inparticular compounds P.01, P.03, P.04, P.06, P.07, P.08, P.11, P.14,P.15, P.16, P.17 and P.19 show an activity of at least 50% at anapplication rate of 200 ppm.

Example B-5 Puccinia recondita: Brown Rust of Wheat, Preventative Test

Puccinia recondita (Brown rust): Wheat leaf segments are placed on agarin multiwell plates (24-well format) and sprayed with the formulated (2%Dimethylsulfoxid, 0.025% Tween 20) test solutions. After drying, theleaf disks are inoculated with a spore suspension of the fungus (45′000conidia/ml). After appropriate incubation, the preventive fungicidalactivity of a compound is assessed 8 days after inoculation as diseasedamage on the leaf disks and calculated as percent efficacy relative tountreated infected control (0=no control of Puccinia recondita,100%=complete control). In this test, compounds listed in Table P aboveshow good activity. In particular compounds P.07, P.11, P.26, P.28,P.29, P.31, P.35, P.51, P.58, P.59, P.61, P.62, P.64, P.70, P.73, P.76,P.77, P.79 and P.82 show an activity of at least 50% at an applicationrate of 200 ppm.

Example B-6 Puccinia recondita: Brown Rust of Wheat, Curative Test

Method Description Puccinia recondita (Brown rust): Wheat leaf segmentsare placed on agar in multiwell plates (24-well format). The leaf disksare then inoculated with a spore suspension of the fungus (45′000conidia/ml). One day after inoculation the formulated (2%Dimethylsulfoxid, 0.025% Tween 20) test solution is applied. Afterappropriate incubation, the curative fungicidal activity of a compoundis assessed 8 days after inoculation as disease damage on the leaf disksand calculated as percent efficacy relative to untreated infectedcontrol (0=no control of Puccinia recondita, 100%=complete control). Inthis test, compounds listed in Table P above show good activity. Inparticular compounds P.26, P.28, P.29, P.31, P.35, P.36, P.41, P.58,P.59, P.61, P.62, P.64, P.69, P.70,P.73, P.76, P.77, P.81 and P.82 showan activity of at least 50% at an application rate of 200 ppm.

Example B-7 Phaeosphaeria nodorum: Septoria Leaf Spot of Wheat,Preventative Test

Method Description Phaeosphaeria nodorum (syn. Septoria nodorum,Leptosphaeria nodorum), glume blotch (Septoria leaf spot): Wheat leafsegments are placed on agar in multiwell plates (24-well format) andsprayed with the formulated (2% Dimethylsulfoxid, 0.025% Tween 20) testsolutions. After drying, the leaf disks are inoculated with a sporesuspension of the fungus (500′000 conidia/ml). After appropriateincubation, the preventive fungicidal activity of a compound is assessed4 days after inoculation as disease damage on the leaf disks andcalculated as percent efficacy relative to untreated infected control(0=no control of Phaeosphaeria nodorum, 100%=complete control). In thistest, compounds listed in Table P above show good activity. Inparticular compounds P.04 and P.29 show an activity of at least 50% atan application rate of 200 ppm.

Example B-8 Magnaporthe grisea: Rice Blast Disease, Preventative Test

Method Description Magnaporthe grisea (syn. Pyricularia oryzae), riceblast disease. Rice leaf segments are placed on agar in multiwell plates(24-well format) and sprayed with the formulated (2% Dimethylsulfoxid,0.025% Tween 20) test solutions. After drying, the leaf disks areinoculated with a spore suspension of the fungus (90′000 conidia/ml).After appropriate incubation, the preventive fungicidal activity of acompound is assessed 5 days after inoculation as disease damage on theleaf disks and calculated as percent efficacy relative to untreatedinfected control (0=no control of Magnaporthe grisea, 100%=completecontrol). In this test, compounds listed in Table P above show goodactivity. In particular compounds P.05, P.08 and P.09 show an activityof at least 50% at an application rate of 200 ppm.

Example B-9 Pyrenophora teres: Net Blotch of Barley, Preventative Test

Method Description Pyrenophora teres (Net blotch): Barley leaf segmentsare placed on agar in multiwell plates (24-well format) and sprayed withthe formulated (2% Dimethylsulfoxid, 0.025% Tween 20) test solutions.After drying, the leaf disks are inoculated with a spore suspension ofthe fungus (25′000 conidia/ml). After appropriate incubation, thepreventive fungicidal activity of a compound is assessed 4 days afterinoculation as disease damage on the leaf disks and calculated aspercent efficacy relative to untreated infected control (0=no control ofPyrenophora teres, 100%=complete control). In this test, compoundslisted in Table P above show good activity. In particular compoundsP.05, P.08, P.09, P.46, P.62, P.64, P.69 and P.73 show an activity of atleast 50% at an application rate of 200 ppm.

What is claimed is:
 1. A compound of formula I

wherein aa) R₁ and R₂, independently from each other, are hydrogen,cyano, formyl, nitro, C₁-C₇alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₇alkylcarbonyl, C₃-C₇alkenylcarbonyl, C₄-C₉cycloalkylcarbonyl,C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkylthio-C₁-C₆alkyl,C₂-C₇alkylcarbonyl-C₁-C₆alkyl, C₃-C₆alkenyloxy-C₁-C₆alkyl,C₃-C₆alkynyloxy-C₁-C₆alkyl, benzyloxy-C₁-C₆alkyl,C₃-C₈cycloalkyl-C₁-C₆alkyl, C₂-C₇alkyloxycarbonyl,C₄-C₇alkenyloxycarbonyl, C₄-C₇alkynyloxycarbonyl,C₄-C₉cycloalkyloxycarbonyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl,C₁-C₆alkylsulfinyl or C₁-C₆haloalkylsulfinyl; or ab) R₁ and R₂,independently from each other, are —Si (R₅₁)(R₅₂)(R₅₃), wherein R₅₁,R₅₂, R₅₃, independently of each other, are halogen, cyano, C₁-C₆alkyl,C₂-C₆alkenyl, C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₂-C₆alkynyl,C₁-C₆alkoxy, benzyl or phenyl; or ac) R₁ and R₂, independently from eachother, are —Si(OR₅₄)(OR₅₅)(OR₅₆), wherein R₅₄, R₅₅, R₅₆, independentlyof each other, are C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₈cycloalkyl,C₃-C₆alkynyl, benzyl or phenyl; or ad) R₁ and R₂, independently fromeach other, are phenylsulfonyl, phenylsufinyl, phenylcarbonyl,phenoxycarbonyl, benzyl, benzylcarbonyl or benzyloxycarbonyl; or ae) R₁and R₂, independently from each other, are phenylsulfonyl,phenylsufinyl, phenylcarbonyl, phenoxycarbonyl, benzyl, benzylcarbonyl,benzyloxycarbonyl mono- to polysubstituted ae1) by substituentsindependently selected from the group consisting of hydroxy, mercapto,halogen, cyano, azido, nitro, —SF₅, amino, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkylthioC₁-C₆alkyl, C₃-C₆alkenyloxy,C₃-C₆haloalkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, benzyloxy, phenoxy, benzyland phenyl, where benzyloxy, phenoxy,benzyl and phenyl for their partmay be mono- to polysubstituted on the phenyl ring by substituentsindependently selected from the group consisting of halogen, cyano,hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or ae2) bysubstituents independently selected from the group consisting ofcarboxy, —C(═O)—Cl, —C(═O)—F, C₂-C₇alkoxycarbonyl,C₂-C₇alkylthiocarbonyl, C₂-C₇haloalkoxycarbonyl,C₃-C₇alkenyloxycarbonyl, C₃-C₇haloalkenyloxycarbonyl,C₃-C₇alkynyloxycarbonyl, benzyloxycarbonyl and phenoxycarbonyl, wherebenzyloxycarbonyl and phenoxycarbonyl for their part may be mono- topolysubstituted on the phenyl ring by substituents independentlyselected form the group consisting of halogen, cyano, hydroxy,C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or ae3) by substituentsindependently selected from the group consisting of formyl,C₂-C₇alkylcarbonyl, C₂-C₇haloalkylcarbonyl, C₃-C₇alkenylcarbonyl,phenylcarbonyl and benzylcarbonyl, where phenylcarbonyl andbenzylcarbonyl for their part may be mono-to polysubstituted on thephenyl ring by substituents independently selected form the groupconsisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy; or ae4) by substituents independently selected from thegroup consisting of aminosulfonyl, C₁-C₆alkylaminosulfonyl,N,N-di(C₁-C₆alkyl)aminosulfonyl, —C(═O)NR₅₇R₅₈, —C(═S)NR₅₇R₅₈ and—NR₅₇R₅₈, wherein R₅₇ and R₅₈, independently of each other, arehydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, phenyl or benzyl,where phenyl, benzyl for their part may be mono- to polysubstituted onthe phenyl ring by substituents independently selected form the groupconsisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy, or R₅₇ and R₅₈ together with their interconnecting nitrogenatom are aziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino,pyrrolidino, imidazolino, imidazolidino, triazolino, tetrazolino,piperazino, piperidino, morpholino, thiomorpholino, each of which, inturn, may be mono- or polysubstituted by substituents selected from thegroup consisting of methyl, halogen, cyano and nitro; and substituentsat nitrogen atoms in the ring systems being other than halogen; or af)either R₁ or R₂ is af1) amino, C₁-C₆alkoxy, C₃-C₆alkenyloxy,C₃-C₈cycloalkyloxy, C₃-C₆alkynyloxy or benzyloxy; or af2) C₁-C₆alkoxy,C₃-C₆alkenyloxy, C₃-C₈cycloalkyloxy, C₃-C₆alkynyloxy, benzyloxy mono- topolysubstituted by substituents independently selected from the groupconsisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxy and C₁-C₆haloalkoxy; or ag) R₁ and R₂, independently fromeach other, are C₁-C₇alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₂-C₇alkylcarbonyl, C₃-C₇alkenylcarbonyl, C₄-C₉cycloalkylcarbonyl,C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkylthio-C₁-C₆alkyl,C₃-C₆alkenyloxy-C₁-C₆alkyl, C₂-C₆alkylcarbonyl-C₁-C₆alkyl,C₃-C₆alkynyloxy-C₁-C₆alkyl, benzyloxy-C₁-C₆alkyl,C₃-C₈cycloalkyl-C₁-C₆alkyl, C₂-C₇alkyloxycarbonyl,C₄-C₇alkenyloxycarbonyl, C₄-C₇alkynyloxycarbonyl orC₄-C₉cycloalkyloxycarbonyl, mono- to polysubstituted by substituentsindependently selected from the group consisting of halogen, cyano,nitro, hydroxy, mercapto, azido, C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₂-C₇alkoxycarbonyl, formyl, C₂-C₇alkylcarbonyl,—Si(R₅₁)(R₅₂)(R₅₃) and —Si(OR₅₄)(OR₅₅)(OR₅₆); or ah) R₁ and R₂,independently from each other, are the group A-; wherein A is a three-to ten-membered monocyclic or fused bicyclic ring system which can bearomatic, partially saturated or fully saturated and can contain 1 to 4hetero atoms selected from the group consisting of nitrogen, oxygen andsulfur, it not being possible for each ring system to contain more than2 oxygen atoms and more than 2 sulfur atoms, and it being possible forthe three- to ten-membered ring system itself to be mono- orpolysubstituted A1) by substituents independently selected from thegroup consisting of fluoro, bromo, iodo, cyano, nitro, hydroxy,mercapto, nitro, azido, formyl, carboxy, —C(═O)—Cl, ═O, ═S, —C(═O)—F,C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₈cycloalkyl,C₅-C₈cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,C₂-C₆haloalkynyl, C₃-C₈halocycloalkyl, C₅-C₈halocycloalkenyl,C₅-C₈halocycloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy,C₃-C₆haloalkenyloxy, C₃-C₆alkynyloxy, C₃-C₈cycloalkyloxy,C₃-C₈halocycloalkyloxy, C₃-C₈cycloalkenyloxy, C₃-C₈halocycloalkenyloxy,benzyloxy and phenoxy, where benzyloxy and phenoxy, in turn, may bemono- to polysubstituted by substituents independently selected from thegroup consisting of halogen, cyano, nitro, hydroxy, mercapto, azido,amino, —SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl andC₁-C₆alkylsulfonyl; or A2) by substituents independently selected fromthe group consisting of HC(═NOR₅₉)—, (C₁-C₆alkyl)C(═NOR₅₉)—,(C₁-C₆haloalkyl)C(═NOR₅₉)—, (C₁-C₆alkyl)C(═NOR₅₉)C₁-C₆alkyl- and(C₁-C₆haloalkyl)C(═NOR₅₉)C₁-C₆alkyl-, wherein R₅₉ is hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, benzyl and phenyl,and benzyl and phenyl mono- to polysubstituted by halogen, cyano,hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₆alkoxy; or A3) bysubstituents independently selected from the group consisting ofC₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, (R₁₄)S(═O)(═NR₁₃)— and (R₁₄)(R₁₅)S(═O)═N—, whereinR₁₃ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl,phenyl or benzyl, or is phenyl or benzyl mono- to polysubstituted byhalogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₆alkoxy, andR₁₄ and R₁₅, independently of each other, are C₁-C₆alkyl,C₃-C₈cycloalkyl, C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl,C₂C₆haloalkenyl, C₂-C₆alkynyl, benzyl or phenyl, or benzyl or phenylindependently of each other, substituted by substituents selected fromthe group consisting of halogen, cyano, hydroxy, C₁-C₆alkyl,C₁-C₆haloalkyl and C₁-C₆alkoxy; or A4) by substituents independentlyselected from the group consisting of —NR₅₇R₅₈, —C(═O)NR₅₇R₅₈ and—C(═S)NR₅₇R₅₈; or A5) by substituents independently selected from thegroup consisting of formyl, C₂-C₇alkylcarbonyl, C₂-C₇haloalkylcarbonyl,C₃-C₇alkenylcarbonyl, C₃-C₇haloalkenylcarbonyl, C₄-C₉cycloalkylcarbonyl,C₄-C₉halocycloalkylcarbonyl, C₂-C₇alkoxycarbonyl,C₂-C₇haloalkoxycarbonyl, C₃-C₇alkenyloxycarbonyl,C₃-C₇alkynyloxycarbonyl, C₄-C₉cycloalkoxycarbonyl,C₂-C₇alkylthiocarbonyl and benzyloxycarbonyl, and benzyloxycarbonylmono- to polysubstituted by substituents independently selected from thegroup consisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyland C₁-C₆alkoxy; or A6) by substituents independently selected from thegroup consisting of —Si(R₅₁)(R₅₂)(R₅₃) and —Si(OR₅₄)(OR₅₅)(OR₅₆); or A7)by substituents independently selected from the group consisting ofaminosulfinyl, (C₁-C₆alkyl)aminosulfonyl,N,N-di(C₁-C₆alkyl)aminosulfonyl, di(C₁-C₆alkyl)amino, (C₁-C₆alkyl)amino,phenyl, phenoxy, benzyl and benzyoxy, where phenyl, phenoxy, benzyl andbenzyloxy for their part may be mono- to polysubstituted on the phenylring by substituents independently selected form the group consisting ofhalogen, cyano, hydroxy, amino, nitro, azido, mercapto, formyl, —SF₅,C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₂-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio,C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio,C₂-C₆alkylcarbonyl-C₁-C₃alkylthio, C₂-C₆alkoxycarbonyl-C₁-C₃6alkylthio,cyano-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,(C₁-C₆alkyl)aminosulfonyl, N,N-di(C₁-C₆alkyl)aminosulfonyl,di(C₁-C₆alkyl)amino and (C₁-C₆alkyl)amino; or ai) R₁ and R₂,independently from each other, are —C(═O)NR₅₇R₅₈; or aj) R₁ and R₂together form a C₂-C₆alkylene bridge which may be mono- topolysubstituted by halogen, cyano, C₁-C₆alkyl or C₁-C₆haloalkyl groups;or ak) R₁ and R₂ together with their interconnecting nitrogen atom arepyrazolino, pyrazolidino, pyrrolino, imidazolino, imidazolidino,triazolino, tetrazolino, piperazino, morpholino, thiomorpholino, each ofwhich, independently of each other, may be mono- to polysubstituted bymethyl groups, halogen, cyano and nitro; or al) the fragment

can be

wherein each of the meanings of said fragment can be mono- topolysubstituted by substituents independently selected from the groupconsisting of halogen, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy; ba) R₃, R₄ and R₇, independently from each other, are ba1)hydrogen, halogen, cyano, nitro, mercapto, hydroxy, azido, —SF₅,—NR₆₄R₆₅, wherein R₆₄ and R₆₅, independently of each other, arehydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, phenyl or benzyl,where phenyl, benzyl for their part may be mono- to polysubstituted onthe phenyl ring by substituents independently selected form the groupconsisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy, or R₆₄ and R₆₅ together with their interconnecting nitrogenatom are aziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino,pyrrolidino, imidazolino, imidazolidino, triazolino, tetrazolino,piperazino, piperidino, morpholino, thiomorpholino, each of which, inturn, may be mono- or polysubstituted by substituents selected from thegroup consisting of methyl, halogen, cyano and nitro; and substituentsat nitrogen atoms in the ring systems being other than halogen; or R₃,R₄ and R₇, independently from each other, are —C(═S)NH₂, —N═C═O, —N═C═S,amino, (R₅₁)(R₅₂)(R₅₃)Si—, (R₅₁)(R₅₂)(R₅₃)Si—(C₁-C₆alkyl)-,(R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-, (OR₅₄)(OR₅₅)(OR₅₆)Si— or(OR₂₁₄)(OR₂₁₅)(OR₂₁₆)Si—(C₁-C₆alkyl)-; wherein R₂₁₄, R₂₁₅ and R₂₁₆independently of each other, are halogen, cyano, C₁-C₆alkyl,C₂-C₆alkenyl, C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₂-C₆alkynyl, benzylor phenyl; or R₃, R₄ and R₇, independently from each other, are ba2)C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,aminosulfinyl, aminosulfonyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkinyloxy,(C₁-C₆alkyl)aminosulfonyl, di(C₁-C₆alkyl)aminosulfonyl, C₁-C₆alkoxy,C₂-C₆alkenyloxy, C₂-C₆alkynyloxy, C₁-C₆alkyl-S(═O)(R₁₄)═N—,(R₁₄)S(═O)(═N—R₁₃)—, (R₁₄)(R₁₅)S(═O)═N—, —S—C₃-C₆-alkenyl,—S—C₃-C₆-alkynyl, —S—C₃-C₈-cycloalkyl, S-benzyl, or —S—C₃-C₆-alkenyl,—S—C₃-C₆-alkynyl, —S—C₃-C₈-cycloalkyl or S-benzyl; all of which can bemono- to polysubstituted by substituents selected from the groupconsisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy; or R₃, R₄ and R₇, independently from each other, are ba3)C₁-C₆alkyl, C₂-C₆alkenyl or C₂-C₆alkynyl, or C₁-C₆alkyl, C₂-C₆alkenyl orC₂-C₆alkynyl mono- to polysubstituted by substituents independentlyselected from the group consisting of halogen, hydroxy, mercapto, cyano,nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆hydroxyalkyl,tri(alkyl)silyl, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl andC₁-C₆haloalkylsulfonyl; or R₃, R₄ and R₇, independently from each other,are ba4) formyl, C₂-C₇alkoxycarbonyl, C₂-C₇haloalkoxycarbonyl,C₃-C₇alkenyloxycarbonyl, C₃-C₇haloalkenyloxycarbonyl,C₂-C₇alkylcarbonyl, carboxy, —C(═O)—Cl, —C(═O)—F,C₂-C₇haloalkylcarbonyl, C₃-C₇alkenylcarbonyl orC₃-C₇haloalkenylcarbonyl; or R₃, R₄ and R₇, independently from eachother, are ba5) phenyl, phenoxy, benzyl or benzyloxy, or phenoxy, benzylor benzyloxy mono- to polysubstituted by substituents independentlyselected from the group consisting of halogen, cyano, nitro, hydroxy,mercapto, azido, amino, —SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl andC₁-C₆alkylsulfonyl; or bb) R₃, R₄ and R₇, independently of each other,are the groups A-, A-O— or A-(C₁-C₆alkyl)-, wherein the group A is asdefined above under ah); ca) R₅ is hydrogen, C₁-C₁₂alkyl, C₂-C₁₂alkenyl,C₂-C₁₂alkynyl, C₁-C₁₂alkylsulfonyl, C₂-C₁₂alkenylsulfonyl,phenylsulfonyl or benzylsulfonyl, or is C₁-C₁₂alkyl, C₂-C₁₂alkenyl,C₂-C₁₂alkynyl, C₁-C₁₂alkylsulfonyl, C₂-C₁₂alkenylsulfonyl,phenylsulfonyl or benzylsulfonyl mono-to polysubstituted by substituentsindependently selected from the group consisting of halogen, cyano,nitro, hydroxy, mercapto, azido, formyl, C₂-C₇alkylcarbonyl,C₂-C₇haloalkylcarbonyl, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl andC₁-C₆alkylsulfonyl; or cb1) R₅ is formyl, C₂-C₁₂alkylcarbonyl,C₃-C₁₂alkenylcarbonyl, C₃-C₁₂alkynylcarbonyl, C₄-C₁₂cycloalkylcarbonyl,benzylcarbonyl, phenylcarbonyl, C₂-C₁₂alkoxycarbonyl,C₄-C₁₂alkenyloxycarbonyl, C₄-C₁₂alkynyloxycarbonyl,C₄-C₁₂cycloalkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl, or iscb2) C₂-C₁₂alkylcarbonyl, C₃-C₁₂alkenylcarbonyl, C₃-C₁₂alkynylcarbonyl,C₄-C₁₂cycloalkylcarbonyl, benzylcarbonyl, phenylcarbonyl,C₂-C₁₂alkoxycarbonyl, C₄-C₁₂alkenyloxycarbonyl,C₄-C₁₂alkynyloxycarbonyl, C₄-C₁₂cycloalkoxycarbonyl, benzyloxycarbonylor phenoxycarbonyl mono- to polysubstituted by substituentsindependently selected from the group consisting of halogen, cyano,C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or cc) R₅ is(R₅₁)(R₅₂)(R₅₃)Si—, (R₅₁)(R₅₂)(R₅₃)Si—(C₁-C₁₂alkyl)-,(R₅₁)(R₅₂)(R₅₃)Si—(C₃-C₈cycloalkyl)-, (R₅₄O)(R₅₅O)(R₅₆O)Si—,(R₅₄O)(R₅₅O)(R₅₆O)Si—(C₁-C₁₂alkyl)- or(R₅₄O)(R₅₅O)(R₅₆O)Si—(C₃-C₈cycloalkyl)-; or cd) R₅ isC₁-C₆alkyl-B—C₁-C₁₂alkyl-, C₂-C₆alkenyl-B—C₁-C₁₂alkyl-,C₂-C₆alkynyl-B—C₁-C₁₂alkyl-, C₃-C₈cycloalkyl-B—C₁-C₁₂alkyl-,benzyl-B—C₁-C₁₂alkyl-, phenyl-B—C₁-C₁₂alkyl-,C₁-C₆alkyl-B—C₂-C₁₂alkenyl-, C₂-C₆alkenyl-B—C₂-C₁₂alkenyl-,C₂-C₆alkynyl-B—C₂-C₁₂alkenyl-, C₃-C₈ycloalkyl-B—C₂-C₁₂alkenyl-,benzyl-B—C₂-C₁₂alkenyl-, phenyl-B—C₂-C₁₂alkenyl-,C₁-C₆alkyl-B—C₂-C₁₂alkynyl-, C₂-C₆alkenyl-B—C₂-C₁₂alkynyl-,C₂-C₆alkynyl-B—C₂-C₁₂alkynyl-, C₃-C₈cycloalkyl-B—C₂-C₁₂alkynyl-,benzyl-B—C₂-C₁₂alkynyl-, phenyl-B—C₂-C₁₂alkynyl-,C₁-C₆alkyl-B—C₃-C₈cycloalkyl-, C₂-C₆alkenyl-B—C₃-C₈cycloalkyl-,C₂-C₆alkynyl-B—C₃-C₈cycloalkyl-, C₃-C₈cycloalkyl-B—C₃-C₈cycloalkyl-,benzyl-B—C₃-C₁₂cycloalkyl- or phenyl-B—C₃-C₁₂cycloalkyl-, wherein thegroup B is —C(═O)—, —C(═S)—, —C(═NOR₅₉)—, —C(R₆₀)═NO—, —ON═C(R₆₀)—,—O—C(═O)—, —C(═O)—O—, —O—, —S—, —S(═O)—, —S(═O)₂—, —S(═O)(═NR₁₃)—,—S(═O)(R₁₄)═N—, —N═S(═O)(R₁₄)—, —N(R₆₂)—C═O)—, —C═O)—N(R₆₂)—,—N(R₆₂)—SO₂— or —SO₂—N(R₆₂)—; cd1) wherein R₆₀ is hydrogen, C₁-C₆alkyl,C₃-C₈cycloalkyl, C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl,C₂-C₆haloalkenyl, C₂-C₆alkynyl, benzyl or phenyl, or benzyl or phenylmono- to polysubstituted by substituents independently selected form thegroup consisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyland C₁-C₆alkoxy, and cd2) R₆₂ is hydrogen, C₁-C₆alkyl, C₃-C₈cycloalkyl,C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, benzylor phenyl, or benzyl or phenyl mono- to polysubstituted by substituentsindependently selected form the group consisting of halogen, cyano,hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or ce) R₅ isC₁-C₆alkyl-B—C₁-C₁₂alkyl-, C₂-C₆alkenyl-B—C₁-C₁₂alkyl-,C₂-C₆alkynyl-B—C₁-C₁₂alkyl-, C₃-C₈cycloalkyl-B—C₁-C₁₂alkyl-,benzyl-B—C₁-C₁₂alkyl-, phenyl-B—C₁-C₁₂alkyl-,C₁-C₆alkyl-B—C₂-C₁₂alkenyl-, C₂-C₆alkenyl-B—C₂-C₁₂alkenyl-,C₂-C₆alkynyl-B—C₂-C₁₂alkenyl-, C₃-C₈cycloalkyl-B—C₂-C₁₂alkenyl-,benzyl-B—C₂-C₁₂alkenyl-, phenyl-B—C₂-C₁₂alkenyl-,C₁-C₆alkyl-B—C₂-C₁₂alkynyl-, C₂-C₆alkenyl-B—C₂-C₁₂alkynyl-,C₂-C₆alkynyl-B—C₂-C₁₂alkynyl-, C₃-C₈cycloalkyl-B—C₂-C₁₂alkynyl-,benzyl-B—C₂-C₁₂alkynyl-, phenyl-B—C₂-C₁₂alkynyl-,C₁-C₆alkyl-B—C₃-C₈cycloalkyl-, C₂-C₆alkenyl-B—C₃-C₈cycloalkyl-,C₂-C₆alkynyl-B—C₃-C₈cycloalkyl-, C₃-C₈cycloalkyl-B—C₃-C₈cycloalkyl-,benzyl-B—C₃-C₁₂cycloalkyl-, phenyl-B—C₃-C₁₂cycloalkyl-, all of which, inturn, are substituted by substituents independently selected from thegroup consisting of halogen, cyano, hydroxy, mercapto, C₁-C₆haloalkyl,C₁-C₆alkoxy, formyl, C₂-C₆alkylcarbonyl, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl and C₁-C₆alkylsulfonyl; or cf) R₅ is A-,A-(C₁-C₆alkyl)-, A-O—(C₁-C₆alkyl)-, A-(C₂-C₆alkenyl)-,A-O—(C₂-C₆alkenyl)-, A-(C₂-C₆-alkynyl)-, A-O—(C₂-C₆alkynyl)-,A-(C₃-C₈cycloalkyl)- or A-O—(C₃-C₈cycloalkyl)-; wherein the group A isas defined above under ah); or cg) R₅ signifies the group —N═C(R₈)R₉;cg1) wherein R₈ and R₉, independently from each other, are hydrogen,halogen, cyano, C₁-C₁₂alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkinyl, C₁-C₁₂alkoxy,formyl, C₂-C₁₂alkylcarbonyl, C₃-C₁₂alkenylcarbonyl, carboxy,C₂-C₁₂alkoxycarbonyl or C₄-C₁₂alkenyloxycarbonyl, or C₁-C₁₂alkyl,C₂-C₁₂alkenyl, C₂-C₁₂alkinyl, C₁-C₁₂alkoxy, C₂-C₁₂alkylcarbonyl,C₃-C₁₂alkenylcarbonyl, C₂-C₁₂alkoxycarbonyl or C₄-C₁₂alkenyloxycarbonylmono- to polysubstituted by substituents independently selected from thegroup consisting of halogen, cyano, nitro, hydroxy, mercapto,C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl and C₁-C₆alkylsulfonyl; or cg2) R₈and R₉ together form a C₂-C₈alkylene bridge which may optionally bemono- to polysubstituted by substituents independently selected from thegroup consisting of halogen, cyano, C₁-C₆alkyl and C₁-C₆haloalkyl; orcg3) R₈ and R₉, independently from each other, are the groups A-, A-O—or A-(C₁-C₆alkyl)-; wherein the group A is as defined above under ah);d) R₆ is hydrogen, fluoro, bromo, chloro, cyano or CHO; or anagronomically acceptable salt, metallic complex, metalloidic complex,isomer, structural isomer, stereo-isomer, diastereoisomer, enantiomer,tautomer or N-oxide thereof.
 2. A compound of formula I according toclaim 1, wherein R₁ and R₂, independently of each other, are hydrogen,cyano, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, benzylor C₂-C₇alkylcarbonyl, each of which may be mono- to polysubstituted bysubstituents independently selected from the group consisting ofhalogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio and C₁-C₆alkoxy; orR₁ and R₂ together form a C₂-C₆alkylene bridge which may be mono- topolysubstituted by methyl groups; or R₁ and R₂ together with theirinterconnecting nitrogen atom are pyrazolino, pyrazolidino, pyrrolino,imidazolino, imidazolidino, triazolino, tetrazolino, piperazino,morpholino, thiomorpholino, each of which, independently of each other,may be mono- to polysubstituted by methyl groups; or R₁ is hydrogen,cyano, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, benzylor C₂-C₇alkylcarbonyl, each of which may be mono- to polysubstituted bysubstituents independently selected from the group consisting ofhalogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio and C₁-C₆alkoxy, andR₂ is amino, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₈cycloalkyloxy orC₃-C₆alkynyloxy; or R₂ is hydrogen, cyano, C₁-C₆alkyl, C₃-C₆cycloalkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, benzyl or C₂-C₇alkylcarbonyl, each of whichmay be mono- to polysubstituted by substituents independently selectedfrom the group consisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkylthio and C₁-C₆alkoxy, and R₁ is hydroxy, amino, C₁-C₆alkoxy,C₃-C₆alkenyloxy, C₃-C₈cycloalkyloxy or C₃-C₆alkynyloxy.
 3. A compound offormula I according to claim 1, wherein R₇ is hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, halogen or cyano.
 4. A compound of formula I accordingto claim 1, wherein R₄ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₇cycloalkyl, halogen, cyano, hydroxy, C₁-C₆alkoxy, amino, azido,mercapto, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, CHO,C₂-C₇alkylcarbonyl, aziridino, azetidino, pyrazolino, pyrazolidino,pyrrolino, pyrrolidino, imidazolino, imidazolidino, triazolino,tetrazolino, piperazino, piperidino, morpholino, thiomorpholino; oraziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino, pyrrolidino,imidazolino, imidazolidino, triazolino, tetrazolino, piperazino,piperidino, morpholino, thiomorpholino, each of which, in turn, is mono-or polysubstituted by substituents selected from the group consisting ofmethyl, halogen; or R₄ is phenyl, or phenyl which is mono- topolysubstituted by substituents independently selected from the groupconsisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy.
 5. A compound of formula I according to claim 1, wherein R₃is hydrogen, C₁-C₆-alkyl, C1-C6-haloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₇cycloalkyl, halogen, cyano, azido, nitro, —N═C═O, —N═C═S,—C(═O)NH₂, —C(═S)NH2, —C(═O)NH(CH₃), —C(═S)NH(CH₃), —C(═O)N(CH₃)₂,—SO₂NH₂, —SO₂NH(CH₃), —SO₂N(CH₃)₂, —C(═S)N(CH₃)₂, —COOH,tri(C₁-C₄alkyl)silyl, tri-(C₁-C₄alkoxy)silyl, hydroxy, C₁-C₆alkoxy,amino, azido, mercapto, C₁-C₆alkylamino, C₂-C₁₂dialkylamino,C₃-C₆alkenylamino, C₆-C₁₂dialkenylamino, C₁-C₆alkylC₃-C₆alkenylamino,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, CHO,C₂-C₇alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₃-C₆alkenyloxycarbonyl,C₃-C₆alkynyloxycarbonyl, phenyl, aziridino, azetidino, pyrazolino,pyrazolidino, pyrrolino, pyrrolidino, imidazolino, imidazolidino,triazolino, tetrazolino, piperazino, piperidino, morpholino orthiomorpholino; or R₃ is aziridino, azetidino, pyrazolino, pyrazolidino,pyrrolino, pyrrolidino, imidazolino, imidazolidino, triazolino,tetrazolino, piperazino, piperidino, morpholino, thiomorpholino mono- orpolysubstituted by substituents independently selected from the groupconsisting of methyl, halogen and phenyl, or by phenyl which itself canbe mono-to polysubstituted by substituents independently selected fromthe group consisting of halogen, cyano, hydroxy, C₁-C₆alkyl,C₁-C₆haloalkyl and C₁-C₆alkoxy; or R₃ is C₁-C₆-alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₃-C₇cycloalkyl, C₁-C₆alkoxy, C₂-C₇alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₃-C₆alkenyloxycarbonyl, C₃-C₆alkynyloxycarbonyl orphenyl, or is phenyl mono- to polysubstituted by substituentsindependently selected from the group consisting of halogen, cyano,nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, hydroxy, C₁-C₆alkoxy, C₁-C₆haloakoxyand phenyl, which phenyl in turn may be mono- to polysubstituted bysubstituents independently selected from the group consisting ofhalogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy. 6.A compound of formula I according to claim 1, wherein R₅ is phenyl,phenyl-C₁-C₁₂alkyl, phenyl-C₃-C₁₂cycloalkyl, phenyl-C₃-C₁₂alkenyl, orphenyl, phenyl-C₁-C₁₂alkyl, phenyl-C₃-C₁₂cyclolkyl, phenyl-C₃-C₁₂alkenylmono- to polysubstituted by substituents independently selected from thegroup consisting of fluoro, bromo, iodo, cyano, nitro, amino, azido,hydroxy, mercapto, trialkylsilyl, trialkoxysilyl, CHO, COOH, C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl,C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy,C₃-C₆alkynyloxy, C₃-C₆cycloalkoxy, C₃-C₆halocycloalkoxy, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl , C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl , C₁-C₆haloalkylsulfonyl, —C(═O)NH₂, —C(═S)NH2,—C(═O)NH(CH₃), —C(═S)NH(CH₃), —C(═O)N(CH₃)₂, —SO₂NH₂, —SO₂NH(CH₃),—SO₂N(CH₃)₂ and —C(═S)N(CH₃)₂.
 7. A compound of formula I according toclaim 1, wherein R₅ is hydrogen, (R₅₁)(R₅₂)(R₅₃)Si—(C₁-C₁₂alkyl)-,triC₁-C₆alkylsilyl, phenyl-diC₁-C₆alkylysilyl, C₁-C₁₂alkyl,C₃-C₁₂alkenyl, C₃-C₁₂alkynyl, C₃-C₁₂cycloalkyl,C₃-C₁₂cycloalkyl-C₁-C₁₂alkyl, C₅-C₁₂cycloalkenyl,C₁-C₁₂alkoxy-C₁-C₁₂alkyl, C₁-C₁₂alkenyloxy-C₁-C₁₂alkyl,C₁-C₁₂alkynyloxy-C₁-C₁₂alkyl, C₁-C₁₂alkylthio-C₁-C₁₂alkyl,C₁-C₁₂alkylsulfenyl-C₁-C₁₂alkyl, C₁-C₁₂alkylsulfonyl-C₀-C₁₂alkyl,C₂-C₁₂alkylcarbonyl-C₀-C₁₂alkyl, C₃-C₁₂alkenylcarbonyl-C₀-C₁₂alkyl,C₂-C₁₂alkoxylcarbonyl-C₀-C₁₂alkyl, C₃-C₁₂alkenyloxycarbonyl-C₀-C₁₂alkylor C₃-C₁₂alkynyloxycarbonyl-C₀-C₁₂alkyl, or R₅ is C₁-C₁₂alkyl,C₃-C₁₂alkenyl, C₃-C₁₂alkynyl, C₃-C₁₂cycloalkyl,C₃-C₁₂cycloalkyl-C₁-C₁₂alkyl, C₅-C₁₂cycloalkenyl,C₁-C₁₂alkoxy-C₁-C₁₂alkyl, C₁-C₁₂alkenyloxy-C₁-C₁₂alkyl,C₁-C₁₂alkynyloxy-C₁-C₁₂alkyl, C₁-C₁₂alkylthio-C₁-C₁₂alkyl,C₁-C₁₂alkylsulfenyl-C₁-C₁₂alkyl, C₁-C₁₂alkylsulfonyl-C₀-C₁₂alkyl,C₂-C₁₂alkylcarbonyl-C₀-C₁₂alkyl, C₃-C₁₂alkenylcarbonyl-C₀-C₁₂alkyl,C₂-C₁₂alkoxylcarbonyl-C₀-C₁₂alkyl, C₃-C₁₂alkenyloxycarbonyl-C₀-C₁₂alkyl,C₃-C₁₂alkynyloxycarbonyl-C₀-C₁₂alkyl mono- to polysubstituted bysubstituents independently selected from the group consisting ofhalogen, cyano, nitro, amino, hydroxy, mercapto, CHO, COOH,C₁-C₆-trialkylsilyl, triC₁-C₆alkoxysilyl, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₁-C₆alkenyl, C₁-C₆haloalkenyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₂-C₇alkylcarbonyl, C₂-C₇alkoxycarbonyl,C₂-C₇alkenyloxycarbonyl, C₂-C₇alkynyloxycarbonyl, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, —C(═O)NH₂, —C(═S)NH₂,—C(═O)NH(CH₃), —C(═S)NH(CH₃) and —C(═O)N(CH₃)₂; and R₅₁, R₅₂, and R₅₃are as defined in claim
 1. 8. A compound of formula I according to claim1, wherein R₁ and R₂, independently of each other, are hydrogen,C₃-C₇cycloalkyl, C₁-C₆alkyl, C₂-C₆alkinyl, hydrogen or pyridine; or R₁and R₂ together with their interconnecting nitrogen atom are pyrrolino;R₃ is hydrogen, C₁-C₆haloalkyl, C₁-C₆alkyl, halogen, cyano, nitro,C₁-C₄alkoxy, phenyl, phenyl substituted by halogen,(R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-, wherein R₅₁, R₅₂ and R₅₃ is asdefined in claim 1; R₄ is hydrogen, halogen, phenyl, imidazolyl, amino,C₁-C₆alkoxy or C₁-C₆alkyl; R₅ is C₁-C₁₂alkyl or the group A, wherein Ais a three- to ten-membered monocyclic or fused bicyclic ring systemwhich can be aromatic, partially saturated or fully saturated and cancontain 1 to 4 hetero atoms selected from the group consisting ofnitrogen, oxygen and sulfur, it not being possible for each ring systemto contain more than 2 oxygen atoms and more than 2 sulfur atoms, and itbeing possible for the three- to ten-membered ring system itself to bemono- or polysubstituted by substituents independently selected from thegroup consisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy andC₁-C₆alkylthio; R₆ is hydrogen; and R₇ is hydrogen or C₁-C₆alkyl.
 9. Acompound of formula I according to claim 8, wherein R₃ is hydrogen,C₁-C₆alkyl, halogen, cyano, nitro, C₁-C₄alkoxy, phenyl, phenylsubstituted by halogen, or (R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-.
 10. Acompound of formula I according to claim 1, wherein R₁ and R₂,independently of each other, are C₁-C₆alkyl, C₃-C₇cycloalkyl,C₂-C₆alkinyl, hydrogen or pyridine; or R₁ and R₂ together with theirinterconnecting nitrogen atom are pyrrolino; R₃ is hydrogen, C₁-C₆alkyl,C₁-C₆alkoxy, C₁-C₆haloalkyl, halogen, cyano, phenyl, phenyl substitutedby halogen, or is (R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-, wherein R₅₁, R₅₂and R₅₃ is as defined in claim 1; R₄ is hydrogen, halogen, C₁-C₆alkoxyor C₁-C₆alkyl; R₅ is C₁-C₆alkyl, phenyl or C₁-C₆alkyl, pyridyl or phenylmono- or disubstituted by substituents selected from the groupconsisting of halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy andC₁-C₆alkylthio; or pyridyl mono- or disubstituted by substituentsselected from the group consisting of fluoro, bromo, iodo, C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy and C₁-C₆alkylthio; R₆ is hydrogen; and R₇is hydrogen or C₁-C₆alkyl.
 11. A compound of formula I according toclaim 10, wherein R₁ and R₂, independently of each other, areC₁-C₆alkyl, C₂-C₆alkinyl, hydrogen or pyridine; or R₁ and R₂ togetherwith their interconnecting nitrogen atom are pyrrolino; R₃ is hydrogen,C₁-C₆alkyl, halogen, cyano, phenyl, phenyl substituted by halogen, or is(R₅₁)(R₅₂)(R₅₃)Si-(C₂-C₆alkinyl)-; R₄ is hydrogen or C₁-C₆alkyl; R₅ isC₁-C₆alkyl, phenyl or pyridyl or phenyl mono- or disubstituted bysubstituents selected from the group consisting of halogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy and C₁-C₆alkylthio or pyridyl mono- ordisubstituted by substituents selected from the group consisting offluoro, bromo, iodo, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy andC₁-C₆alkylthio.
 12. A compound of formula X

wherein aa) R₁ and R₂, independently from each other, are hydrogen,cyano, formyl, nitro, C₁-C₇alkyl, C₂-C₆alkenyl C₂-C₆alkynylC₂-C₇alkenylcarbonyl C₃-C₇alkenylcarbonyl C₄-C₉cycloalkylcarbonyl,C₁-C₆alkoxy -C₁-C₆alkyl, C₁-C₆alkylthio-C₁-C₆alkyl,C₂-C₇alkylcarbonyl-C₁-C₆alkyl, C₃C₆alkenyloxy-C₁-C₆alkyl,C₃-C₆alkynyloxy-C₁-C₆alkyl, benzyloxy-C₁-C₆alkyl,C₃-C₈cycloalkyl-C₁-C₆alkyl, C₂-C₇alkyloxycarbonyl,C₄-C₇alkenyloxycarbonyl, C₄-C₇alkynyloxycarbonyl,C₄-C₉cycloalkyloxycarbonyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl,C₁-C₆alkylsulfinyl or C₁-C₆haloalkylsulfinyl; or ab) R₁ and R₂,independently from each other, are —Si(R₅₁)(R₅₂)(R₅₃), wherein R₅₁ ,R₅₂, R₅₃, independently of each other, are halogen, cyano, C₁-C₆alkyl,C₂-C₆alkynyl, C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₂-C₆alkynylC₁-C₆alkoxy, benzyl or phenyl; or ac) R₁ and R₂, independently from eachother, are —Si(OR₅₄)(R₅₅)(R₅₆), wherein R₅₄, R₅₅, R₅₆, independently ofeach other, are C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₈cycloalkyl, C₃-C₆alkynyl,benzyl or phenyl; or ad) R₁ and R₂ independently from each other, arephenylsulfonyl, phenylsufinyl phenylcarbonyl, phenoxycarbonyl, benzyl,benzylcarbonyl or benzyloxycarbonyl; or ae) R₁ and R₂ independently fromeach other, are phenylsulfonyl, phenylsufinyl phenylcarbonyl,phenoxycarbonyl, benzyl, benzylcarbonyl, benzyloxycarbonyl mono- topolysubstituted ae1) by substituents independently selected from thegroup consisting of hydroxy, mercapto, halogen, cyano, azido, nitro,—SF₅ amino C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl,C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl,C₂C₆haloalkynyl C₁-C₆alkoxy C₁-C₆haloalkoxy C₁-C₆alkoxy C₁-C₆alkyl,C₁-C₆alkylthioC₁-C₆alkyl, C₃C₆alkenyloxy C₃-C₆haloalkenyloxyC₃-C₆alkynyloxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinylC₁-C₆haloalkylsulfinyl C₁-C₆alkylsulfonyl C₁-C₆haloalkylsulfonyl,benzyloxy, phenoxy, benzyl and phenyl, where benzyloxy, phenoxy, benzyland phenyl for their part may be mono- to polysubstituted on the phenylring by substituents independently selected from the group consisting ofhalogen, cyano, hydroxy, C₁-C₆ alkyl, C₁-C₆haloalkoxy and C-₁-C₆alkoxy;or ae2) by substituents independently selected from the group consistingof carboxy, —C(═O)—Cl, —C(═O)—F C₂-C₇alkoxycarbonylC₂-C₇alkylthiocarbonyl, C₂-C₇haloalkoxycarbonyl,C₃-C₇alkenyloxycarbonyl, C₃-C₇haloalkenyloxycarbonyl,C₃-C₇alkynyloxycarbonyl, benzyloxycarbonyl and phenoxycarbonyl, wherebenzyloxycarbonyl and phenoxycarbonyl for their part may be mono- topolysubstituted on the phenyl ring by substituents independentlyselected form the group consisting of halogen, cyano, hydroxy,C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or ae3) by substituentsindependently selected from the group consisting of formyl,C₂-C₇alkylcarbonyl, C₂-C₇haloalkylcarbonyl, C₃-C₇alkenylcarbonyl,phenylcarbonyl and benzylcarbonyl, where phenylcarbonyl andbenzylcarbonyl for their part may be mono- to polysubstituted on thephenyl ring by substituents independently selected form the groupconsisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy; or ae4) by substituents independently selected from thegroup consisting of aminosulfonyl, C₁-C₆alkylaminosulfonyl, NN-di(C₁-C₆alkyl)aminosulfonyl, —C(═O)NR₅₇R₅₈, —C(═S)NR₅₇R₅₈ and —NR₅₇R₅₈wherein R₅₇ and R₅₈, independently of each other are hydrogenC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl C₃-C₆haloalkenyl C₃-C₆alkynylC₃-C₈cycloalkyl, C₃-C₈halocycloalkyl,I phenyl or benzyl, where phenyl,benzyl for their part may be mono- to polysubstituted on the phenyl ringby substituents independently selected form the group consisting ofhalogen, cyano, hydroxy, C-₁-C₆alkyl, C-₁-C₆haloalkyl and C₁-C₆alkoxy,or R₅₇ and R₅₈ together with their interconnecting nitrogen atom areaziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino, pyrrolidino,imidazolino, imidazolidino, triazolino, tetrazolino, piperazino,piperidino, morpholino, thiomorpholino, each of which, in turn, may bemono- or polysubstituted by substituents selected from the groupconsisting of methyl, halogen, cyano and nitro; and substituents atnitrogen atoms in the ring systems being other than halogen; or af)either R₁ or R₂ is af1) amino, C₁-C₆alkoxy C₃-C₆alkenyloxyC₃-C₈cycloalkyloxy, C₃-C₆alkynyloxy, or benzyloxy; or af2) C₁-C₆alkoxyC₃-C₆alkenyloxy C₃-C₈cycloalkyloxy C₃-C₆alkynvloxy, benzyloxy mono- topolysubstituted by substituents independently selected from the groupconsisting of halogen, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxyand C₁-C₆haloalkoxy; or ag) R-₁ and R₂, independently from each other,are C₁-C₇alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₇alkylcarbonylC₃-C₇alkenylcarbonyl C₄-C₉cycloalkylcarbonyl, C₁-C₆alkoxy -C₁-C₆alkyl,C₁-C₆alkylthio-C₁-C₆alkyl, C₃-C₆alkenyloxy-C₁-C₆alkyl,C₂-C₆alkylcarbonyl-C₁-C₆alkyl, C₃-C₆alkynyloxy-C₁-C₆alkyl,benzyloxy-C₁-C₆alkyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₂-C₇alkyloxycarbonyl,C₄-C₇alkenyloxycarbonyl, C₄-C₇alkynyloxycarbonyl orC₄-C₉cycloalkyloxycarbonyl, mono- to polysubstituted by substituentsindependently selected from the group consisting of halogen, cyano,nitro, hydroxy, mercapto, azido, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxyC₁-C₆haloalkoxy C₁-C₆alkylthio, C₁-C₆alkylsulfinyl C₁-C₆alkylsulfonyl,C₂-C₇alkoxycarbonyl, formyl, C₂-C₇alkylcarbonyl, —Si(R₅₁)(R₅₂)(R₅₃) and—Si(OR₅₄)(OR₅₅)(OR₅₆); or ah) R₁ and R₂ independently from each otherare the group A-; wherein A is a three- to ten-membered monocyclic orfused bicyclic ring system which can be aromatic, partially saturated orfully saturated and can contain 1 to 4 hetero atoms selected from thegroup consisting of nitrogen, oxygen and sulfur, it not being possiblefor each ring system to contain more than 2 oxygen atoms and more than 2sulfur atoms, and it being possible for the three- to ten-membered ringsystem itself to be mono- or polysubstituted A1) by substituentsindependently selected from the group consisting of fluoro, bromo, iodo,cyano, nitro, hydroxy, mercapto, nitro, azido, formyl, carboxy,—C(═O)—Cl, ═O,═S, —C(═O)—F, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl C₅-C₈cycloalkynyl, C₁-C₆haloalkyl,C₂-C₆haloalkenylyl C₂-C₆haloalkynyl C₃-C₈halocycloalkyl,C₅-C₈halocycloalkenyl C₅-C₈halocycloalkynyl C₁-C₆alkoxy C₁-C₆haloalkoxyC₃-C₆alkenyloxy, C₃-C₆haloalkenylyloxy C₃-C₆alkynyloxy,C₃-C₈cycloalkyloxy C₃-C₈halocycloalkyloxy, C₃-C₈cycloalkenyloxy,C₃-C₈halocycloalkenyloxy, benzvloxv phenoxy, where benzvloxv andphenoxy, in turn, may be mono- to polysubstituted by substituentsindependently selected from the group consisting of halogen, cyano,nitro, hydroxy, mercapto, azido, amino, —SF_(S), C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkoxyC₁-C₆alkyl,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl and C₁-C₆alkylsulfonyl; or A2) bysubstituents independently selected from the group consisting ofHC(═NOR₅₉)—, (C₁-C₆alkyl)C(═NOR₅₉)—, (C₁-C₆haloalkyl)C(═NOR₅₉)—,(C₁-C₆alkyl)C(═NOR₅₉)C₁-C₆alkyl- and(C₁-C₆haloalkyl)C(═NOR₆₉K₁-C₆alkyl-, wherein R₅₉ is hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenylyl,C₃-C₆alkynyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, benzyl and phenyl,and benzyl and phenyl mono- to polysubstituted by halogen, cyano,hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₆alkoxy; or A3) bysubstituents independently selected from the group consisting ofC₂-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinylC₁-C₆alkylsulfonyl (R₁₄)S(═O)(═NR₁₃)— and (R₁₄ )(R₁₅)S(═O)═N—, whereinR₁₃ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl,C₃-C₆haloalkenylyl, C₃-C₆alkynyl, C₃-C₈cycloalkyl, C₃-C₈halocvcloalkvl,phenyl or benzyl, or is phenyl or benzyl mono- to polysubstituted byhalogen, cyano, hydroxyl, C₁-C₆alkyl, C₁-C₆haloalkyl, or C₁-C₆alkoxy,and R₁₄ and R₅, independently of each other, are C₁-C₆alkyl,C₃-C₈cycloalkyl, C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenylC₂-C₆haloalkenyl C₂-C₆alkynyl, benzyl or phenyl, or benzyl or phenylindependently of each other, substituted by substituents selected fromthe group consisting of halogen, cyano, hydroxyl, C₁-C₆alkyl,C₁-C₆haloalkyl and C₁-C₆alkoxy; or A4) by substituents independentlyselected from the group consisting of —NR₅₇R₅₈, —C(═O)NR₅₇R₅₈ and—C(═S)NR₅₇R₅₈ or A5) by substituents independently selected from thegroup consisting of formyl, C₂-C₇alkylcarbonyl, C₂-C₇haloalkylcarbonyl,C₃-C₇alkenylcarbonyl, C₃-C₇haloalkenylylcarbonyl,C₄-C₉cycloalkylcarbonyl, C₄-C₉halocycloalkylcarbonyl,C₂-C₇alkoxycarbonyl, C₂-C₇haloalkoxycarbonyl, C₃-C₇alkenyloxycarbonyl,C₃-C₇alkynyloxycarbonyl, C₄-C₉cycloalkoxycarbonyl,C₂-C₇alkylthiocarbonyl and benzyloxycarbonyl, and benzyloxycarbonylmono- to polysubstituted by substituents independently selected from thegroup consisting of halogen, cyano, hydroxyl, C₁-C₆haloalkyl andC-₁-C₆alkoxy; or A6) by substituents independently selected from thegroup consisting of —Si(R₅₁)(R₅₂)(R₅₃) and —Si(OR₅₄ OR₅₅)(OR₅₆); or A7)by substituents independently selected from the group consisting ofaminosulfinyl, (C₁-C₆alkyl)aminosulfonyl,N,N-di(C₁-C₆alkyl)aminosulfonyl, di(C₁-C₆alkyl)amino, (C₁-C₆alkyl)amino,phenyl, phenoxy, benzyl and benzyoxy, where phenyl, phenoxy, benzyl andbenzyloxy for their part may be mono- to polysubstituted on the phenylring by substituents independently selected form the group consisting ofhalogen, cyano, hydroxy, amino, nitro, azido, mercapto, formyl, —SF₅,C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₂-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio,C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio,C₂-C₆alkylcarbonyl-C₁-C₃alkylthio, C₂-C₆alkoxycarbonyl-C₁-C₃6alkylthio,cyano-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,(C₁-C₆alkyl)aminosulfonyl, N,N-di(C₁-C₆alkyl)aminosulfonyl,di(C₁-C₆alkyl)amino and (C₁-C₆alkyl)amino; or ai) R₁ and R₂,independently from each other, are —C(═O)NR₅₇R₅₈; or aj) R₁ and R₂together form a C₂-C₆alkylene bridge which may be mono- topolysubstituted by halogen, cyano, C₁-C₆alkyl or C₁-C₆haloalkyl groups;or ak) R₁ and R₂ together with their interconnecting nitrogen atom arepyrazolino, pyrazolidino, pyrrolino, imidazolino, imidazolidino,triazolino, tetrazolino, piperazino, morpholino, thiomorpholino, each ofwhich, independently of each other, may be mono- to polysubstituted bymethyl groups, halogen, cyano and nitro; or al) the fragment

 can be

wherein each of the meanings of said fragment can be mono- topolysubstituted by substituents independently selected from the groupconsisting of halogen, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy; ba) R₃, R₄ and R₇, independently from each other, are ba1)hydrogen, halogen, cyano, nitro, mercapto, hydroxy, azido, —SF₅,—NR₆₄R₆₅, wherein R₆₄ and R₆₅, independently of each other, arehydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, phenyl or benzyl,where phenyl, benzyl for their part may be mono- to polysubstituted onthe phenyl ring by substituents independently selected form the groupconsisting of halogen, cyano, hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy, or R₆₄ and R₆₅ together with their interconnecting nitrogenatom are aziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino,pyrrolidino, imidazolino, imidazolidino, triazolino, tetrazolino,piperazino, piperidino, morpholino, thiomorpholino, each of which, inturn, may be mono- or polysubstituted by substituents selected from thegroup consisting of methyl, halogen, cyano and nitro; and substituentsat nitrogen atoms in the ring systems being other than halogen; or R₃,R₄ and R₇, independently from each other, are —C(═S)NH₂, —N═C═O, —N═C═S,amino, (R₅₁)(R₅₂)(R₅₃)Si—, (R₅₁)(R₅₂)(R₅₃)Si—(C₁-C₆alkyl)-,(R₅₁)(R₅₂)(R₅₃)Si—(C₂-C₆alkinyl)-, (OR₅₄)(OR₅₅)(OR₅₆)Si— or(OR₂₁₄)(OR₂₁₅)(OR₂₁₆)Si—(C₁-C₆alkyl)-; wherein R₂₁₄, R₂₁₅ and R₂₁₆independently of each other, are halogen, cyano, C₁-C₆alkyl,C₂-C₆alkenyl, C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₂-C₆alkynyl, benzylor phenyl; or R₃, R₄ and R₇, independently from each other, are ba2)C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,aminosulfinyl, aminosulfonyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkinyloxy,(C₁-C₆alkyl)aminosulfonyl, di(C₁-C₆alkyl)aminosulfonyl, C₁-C₆alkoxy,C₂-C₆alkenyloxy, C₂-C₆alkynyloxy, C₁-C₆alkyl-S(═O)(R₁₄)═N—,(R₁₄)S(═O)(═N—R₁₃)—, (R₁₄)(R₁₅)S(═O)═N—, —S—C₃-C₆-alkenyl,—S—C₃-C₆-alkynyl, —S—C₃-C₈-cycloalkyl, S-benzyl, or —S—C₃-C₆-alkenyl,—S—C₃-C₆-alkynyl, —S—C₃-C₈-cycloalkyl or S-benzyl; all of which can bemono- to polysubstituted by substituents selected from the groupconsisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy; or R₃, R₄ and R₇, independently from each other, are ba3)C₁-C₆alkyl, C₂-C₆alkenyl or C₂-C₆alkynyl, or C₁-C₆alkyl, C₂-C₆alkenyl orC₂-C₆alkynyl mono- to polysubstituted by substituents independentlyselected from the group consisting of halogen, hydroxy, mercapto, cyano,nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆hydroxyalkyl,tri(alkyl)silyl, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl andC₁-C₆haloalkylsulfonyl; or R₃, R₄ and R₇, independently from each other,are ba4) formyl, C₂-C₇alkoxycarbonyl, C₂-C₇haloalkoxycarbonyl,C₃-C₇alkenyloxycarbonyl, C₃-C₇haloalkenyloxycarbonyl,C₂-C₇alkylcarbonyl, carboxy, —C(═O)—Cl, —C(═O)—F,C₂-C₇haloalkylcarbonyl, C₃-C₇alkenylcarbonyl orC₃-C₇haloalkenylcarbonyl; or R₃, R₄ and R₇, independently from eachother, are ba5) phenyl, phenoxy, benzyl or benzyloxy, or phenoxy, benzylor benzyloxy mono- to polysubstituted by substituents independentlyselected from the group consisting of halogen, cyano, nitro, hydroxy,mercapto, azido, amino, —SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl andC₁-C₆alkylsulfonyl; or bb) R₃, R₄ and R₇, independently of each other,are the groups A-, A-O— or A-(C₁-C₆alkyl)-, wherein the group A is asdefined above under ah); d) R6 is hydrogen, fluoro, bromo, chloro, cyanoor CHO; and R₁₀₀ is SH—, nitro, halogen, imidazolyl, triazolyl,C₁-C₆alkylthio, C₁-C₆alkylsulfenyl or C₁-C₆alkysulfonyl.
 13. A method ofcontrolling or preventing infestation of useful plants byphytopathogenic microorganisms, wherein a compound of formula Iaccording to claim 1 or a composition, comprising this compound asactive ingredient, is applied to the plants, to parts thereof or thelocus thereof.
 14. A composition for controlling and protecting againstphytopathogenic microorganisms, comprising a compound of formula Iaccording to claim 1 and an inert carrier.